RSS-Feed abonnieren
DOI: 10.1055/s-0028-1083210
Cobalt-Catalysed Carbon-Carbon Bond-Formation Reactions
Publikationsverlauf
Publikationsdatum:
27. Oktober 2008 (online)

Abstract
The recent developments in cobalt catalysis are compiled in this review covering the years 2000 through 2007. Special focus is directed towards cobalt-catalysed ring-formation reactions as well as towards cobalt-catalysed (cross-) coupling reactions and synthetically useful applications thereof in the synthesis of acyclic compounds.
1 Introduction
2 Cobalt-Catalysed Cycloaddition Reactions
2.1 Cyclopropanation
2.2 Four-Membered-Ring Formation
2.3 Five-Membered-Ring Formation
2.4 Six-Membered-Ring Formation
2.5 Seven-Membered-Ring Formation
2.6 Eight-Membered-Ring Formation
2.7 Ten-Membered-Ring Formation
3 Cobalt-Catalysed Synthesis of Acyclic Compounds
3.1 Coupling Reactions between Alkenes and Alkynes
3.2 Cross-Coupling Reactions
3.3 Cobalt-Catalysed Coupling Reactions Using Grignard Reagents
3.4 Hydrocyanation, Hydrophosphination, Hydrosilylation and Hydrovinylation Reactions
3.5 Nucleophilic Substitution with Organocobalt Reagents
3.6 Cobalt-Catalysed Carbonylative Ring-Expansion and Ring-Opening Reactions
4 Miscellaneous
5 Conclusions and Outlook
Key words
catalysis - cobalt - coupling reaction - cyclisation - 1,4-dienes - ring expansion
- 1a
Omae I. Appl. Organomet. Chem. 2007, 21: 318 - 1b
Laschat S.Becheanu A.Bell T.Baro A. Synlett 2005, 2547 - 1c
Varela JA.Saá C. Chem. Rev. 2003, 103: 3787 - 2a
Agenet N.Buisine O.Slowinski F.Gandon V.Aubert C.Malacria M. In Organic Reactions Vol. 68:RajanBabu TV. Wiley; New York: 2007. p.1 - 2b
Gandon V.Aubert C.Malacria M. Curr. Org. Chem. 2005, 9: 1699 - 2c
Malacria M.Aubert C.Renaud JL. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 1:Lautens M.Trost BM. Thieme; Stuttgart: 2001. p.439 - 2d
Welker ME. Curr. Org. Chem. 2001, 5: 785 - 2e
Saito S.Yamamoto Y. Chem. Rev. 2000, 100: 2901 - 2f
Ojima I.Tzamarioudaki M.Li Z.Donovan RJ. Chem. Rev. 1996, 96: 635 - 2g
Lautens M.Klute W.Tam W. Chem. Rev. 1996, 96: 49 - 2h
Grotjahn DB. In Comprehensive Organometallic Chemistry II Vol. 12:Abel EW.Stone FGA.Wilkinson G.Hegedus L. Pergamon Press; Oxford: 1995. p.741 - 2i
Schore NE. In Comprehensive Organic Synthesis Vol. 5:Trost BM.Fleming I.Paquette LA. Pergamon Press; Oxford: 1991. p.1129 - 2j
Vollhardt KPC. Angew. Chem., Int. Ed. Engl. 1984, 23: 539 ; Angew. Chem. 1984, 96, 525 - 3a
Davies HML.Bruzinski PR.Lake DH.Kong N.Fall MJ. J. Am. Chem. Soc. 1996, 118: 6897 - 3b
Nishiyama H.Itoh Y.Matsumoto H.Park S.-B.Itoh K. J. Am. Chem. Soc. 1994, 116: 2223 - 3c
Doyle MP.Winchester WR.Hoorn JAA.Lynch V.Simonsen SH.Ghosh R. J. Am. Chem. Soc. 1993, 115: 9968 - 3d
Evans DA.Woerpel KA.Scott MJ. Angew. Chem., Int. Ed. Engl. 1992, 31: 430 ; Angew. Chem. 1992, 104, 439 - 3e
Fritschi H.Leutenegger U.Pfaltz A. Angew. Chem., Int. Ed. Engl. 1986, 25: 1005 ; Angew. Chem. 1986, 98, 1028 - 3f
Nakamura A.Konishi A.Tsujitani R.Kudo M.-A.Otsuka S. J. Am. Chem. Soc. 1978, 100: 3449 - 3g
Nozaki H.Moriuti S.Takaya H.Noyori R. Tetrahedron 1968, 24: 3655 - 4a
Omura K.Uchida T.Irie R.Katsuki T. Chem. Commun. 2004, 2060 - 4b
Katsuki T. J. Mol. Catal. A: Chem. 1996, 113: 87 - 5a
Shitama H.Katsuki T. Chem. Eur. J. 2007, 13: 4849 - 5b
Uchida T.Katsuki T. Synthesis 2006, 1715 - 5c
Uchida T.Saha B.Katsuki T. Tetrahedron Lett. 2001, 42: 2521 - 5d
Ito YN.Katsuki T. Bull. Chem. Soc. Jpn. 1999, 72: 603 - 6a
Niimi T.Uchida T.Irie R.Katsuki T. Adv. Synth. Catal. 2001, 343: 79 - 6b
Niimi T.Uchida T.Irie R.Katsuki T. Tetrahedron Lett. 2000, 41: 3647 - 7
Gao J.Woolley FR.Zingaro RA. Org. Biomol. Chem. 2005, 3: 2126 - 8
Wurz RP.Charette AB. Org. Lett. 2002, 4: 4531 - 9a
Ikeno T.Nishizuka A.Sato M.Yamada T. Synlett 2001, 406 - 9b
Ikeno T.Sato M.Sekino H.Nishizuka A.Yamada T. Bull. Chem. Soc. Jpn. 2001, 74: 2139 - 10
Shepperson I.Quici S.Pozzi G.Nicoletti M.O’Hagan D. Eur. J. Org. Chem. 2004, 4545 - 11a
Chen Y.Fields KB.Zhang XP. J. Am. Chem. Soc. 2004, 126: 14718 - 11b
Huang L.Chen Y.Gao G.-Y.Zhang XP. J. Org. Chem. 2003, 68: 8179 - 12
Chen Y.Zhang XP. Synthesis 2006, 1697 - 13
Chen Y.Zhang XP. J. Org. Chem. 2007, 72: 5931 - 14
Chen Y.Ruppel JV.Zhang XP. J. Am. Chem. Soc. 2007, 129: 12074 - 15
Caselli A.Gallo E.Ragaini F.Ricatto F.Abbiati G.Cenini S. Inorg. Chim. Acta 2006, 359: 2924 - 16 For an accumulation of cyclobutane
synthesis in the total synthesis of pentacycloanammoxic acid, see:
Mascitti V.Corey EJ. J. Am. Chem. Soc. 2004, 126: 15664 - 17a
Baik T.-G.Luis AL.Wang L.-C.Krische MJ. J. Am. Chem. Soc. 2001, 123: 6716 - 17b
Wang L. C.Jang H.-Y.Roh Y.Lynch V.Schultz A. J.Wang X.Krische MJ. J. Am. Chem. Soc. 2002, 124: 9448 - 18a
Ishii Y.Kawahara M.Noda T.Ishigaki H.Ogawa M. Bull. Chem. Soc. Jpn. 1983, 56: 2181 - 18b
Saito S.Hirayama K.Kabuto C.Yamamoto Y. J. Am. Chem. Soc. 2000, 122: 10776 - 19a
See ref. 2g
- 19b
Schore NE. Chem. Rev. 1988, 88: 1081 - 20
Chao KC.Rayabarapu DK.Wang C.-C.Cheng C.-H. J. Org. Chem. 2001, 66: 8804 - 21
Treutwein J.Hilt G. Angew. Chem. Int. Ed. 2008, 47: 6811; Angew. Chem. 2008, 120, 6916 - 22a
Benisch C.Werz DB.Gleiter R.Rominger F.Oeser T. Eur. J. Inorg. Chem. 2003, 1099 - 22b
Haberhauer G.Rominger F.Gleiter R. Angew. Chem. Int. Ed. 1998, 37: 3376 ; Angew. Chem. 1998, 110, 3632 - 23a
Lee SI.Son SU.Choi MR.Chung YK.Lee S.-G. Tetrahedron Lett. 2003, 44: 4705 - 23b
Son SU.Chung YK. J. Org. Chem. 2000, 65: 6142 - 23c
Son SU.Choi DS.Chung YK.Lee S.-G. Org. Lett. 2000, 2: 2097 - 24
Chang H.-T.Jayanth TT.Cheng C.-H. J. Am. Chem. Soc. 2007, 129: 4166 - 25a
Synthetic
Application of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles
and Natural Products
Padwa A.Pearson PW. Wiley; New York: 2002. - 25b
Trossell KBG. In Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis VCH; New York: 1988. - 25c
Tufariello JJ. In 1,3-Dipolar Cycloaddition Chemistry Vol. 2:Padwa A. Wiley; New York: 1984. p.83 - 26a
Desimoni G.Faita G.Mella M.Boiocchi M. Eur. J. Org. Chem. 2005, 1020 - 26b
Desimoni G.Faita G.Mella M.Righetti P.Zema M. Tetrahedron 1999, 55: 8509 - 27
Shirahase M.Kanemasa S.Hasegawa M. Tetrahedron Lett. 2004, 45: 4061 - 28
Suga H.Kakehi A.Ito S.Sugimoto H. Bull. Chem. Soc. Jpn. 2003, 76: 327 - 29a
Kezuka S.Ohtsuki N.Mita T.Kogami Y.Ashizawa T.Ikeno T.Yamada T. Bull. Chem. Soc. Jpn. 2003, 76: 327 - 29b
Ohtsuki N.Kezuka S.Kogami Y.Mita T.Ashizawa T.Ikeno T.Yamada T. Synthesis 2003, 1462 - 29c
Mita T.Ohtsuki N.Ikeno T.Yamada T. Org. Lett. 2002, 4: 2457 - 30
Huang ZZ.Kang J.-B.Zhou J.Ye M.-C.Tang Y. Org. Lett. 2004, 6: 1677 - 31a
Carmona D.Lamata MP.Oro LA. Coord. Chem. Rev. 2000, 200-202: 717 - 31b
Evans DA.Johnson JS. In Comprehensive Asymmetric Catalysis Vol. III:Jacobson EN.Pfaltz A.Yamamoto H. Springer; Berlin: 1999. Chap. 33.1. - 31c
Kagan HB.Riant O. Chem. Rev. 1992, 92: 1007 - 32a
Sibi MP.Manyem S.Palencia H. J. Am. Chem. Soc. 2006, 128: 13660 - 32b
Zendehdel M.Foroghi Far N.Gaykani Z. J. Inclusion Phenom. Macrocyclic Chem. 2005, 53: 4749 - 32c
Mahindaratne MPD.Quinones BA.Recio A.Rodriguez EA.Lakner FJ.Negrete GR. Tetrahedron 2005, 61: 9495 - 32d
Desimoni G.Faita G.Guala M.Pratelli C. Tetrahedron 2002, 58: 2929 - 32e
Ghosh AK.Cho H.Cappiello J. Tetrahedron: Asymmetry 1998, 9: 2271 - 32f
Kanemasa S.Oderaotoshi Y.Sakaguchi S.-I.Yamamoto H.Tanaka J.Wada E.Curran DP. J. Am. Chem. Soc. 1998, 120: 3074 - 33
Suga H.Kakehi A.Mitsuda M. Bull. Chem. Soc. Jpn. 2004, 77: 561 - 34a
Gilvra JD.Rawal VH. Synlett 2004, 2440 - 34b
Huang Y.Iwama T.Rawal VH. J. Am. Chem. Soc. 2002, 124: 5950 - 35a
Simonsen KB.Svenstrup N.Roberson N.Jørgensen KA. Chem. Eur. J. 2000, 5: 123 - 35b
Furuno H.Hanamoto T.Sugimoto Y.Inanaga J. Org. Lett. 2000, 2: 49 - 35c
Dossetter AG.Jamison TF.Jacobsen EN. Angew. Chem. Int. Ed. 1999, 38: 2398 ; Angew. Chem. 1999, 111, 2549 - 35d
Mikami K.Matsukawa S. Nature 1997, 385: 613 - 35e
Motoyama Y.Mikami K. J. Chem. Soc., Chem. Commun. 1994, 1563 - 36
Iwakura I.Ikeno T.Yamada T. Angew. Chem. Int. Ed. 2005, 44: 2524 ; Angew. Chem. 2005, 117, 2580 - 37a
Kwiatkowski P.Chaadaj W.Malinowsk M.Asztemborska M.Jurczak J. Tetrahedron: Asymmetry 2005, 16: 2959 - 37b
Malinowska M.Kwiatkowski P.Jurczak J. Tetrahedron Lett. 2004, 45: 7693 - 38
Kezuka S.Mita T.Ohtsuki N.Ikeno T.Yamada T. Bull. Chem. Soc. Jpn. 2001, 74: 1333 - 39a
Hu Y.-J.Huang X.-D.Yao Z.-J.Wu Y.-L. J. Org. Chem. 1998, 63: 2456 - 39b
Li L.-S.Wu Y.Hu Y.-J.Xia L.-J.Wu Y.-L. Tetrahedron: Asymmetry 1998, 9: 3687 - 40
Degl’Innocenti A.Capperucci A.Nocentini T.Biondi S.Fratini V.Castagnoli G.Malesci I. Synlett 2004, 2159 - 41a
Hilt G.Lüers S.Schmidt F. Synthesis 2003, 634 - 41b
Hilt G.Korn TJ. Tetrahedron Lett. 2001, 42: 2783 - 41c
Hilt G.du Mesnil F.-X. Tetrahedron Lett. 2000, 41: 6757 - 42
Hilt G.Smolko KI.Lotsch BV. Synlett 2002, 1081 - 43
Hilt G.Janikowski J.Hess W. Angew. Chem. Int. Ed. 2006, 45: 5204 ; Angew. Chem. 2006, 118, 5328 - 44
Mörschel P.Janikowski J.Hilt G.Frenking G. J. Am. Chem. Soc. 2008, 130: 8952 - 45a
Hilt G.Lüers S.Harms K. J. Org. Chem. 2004, 69: 624 - 45b
Hilt G.Lüers S. Synthesis 2003, 1784 - 46a
Hilt G.Hengst C. J. Org. Chem. 2007, 72: 7337 - 46b
Hilt G.Hengst C. Synlett 2006, 3247 - 47
Hilt G.Smolko KI. Synthesis 2002, 686 - 48
Hilt G.Korn TJ.Smolko KI. Synlett 2003, 241 - 49a
Hilt G.Galbiati F. Org. Lett. 2006, 8: 2195 - 49b
Hilt G.Galbiati F. Synthesis 2006, 3589 - 50
Hilt G.Smolko KI. Angew. Chem. Int. Ed. 2003, 42: 2795 ; Angew. Chem. 2003, 115, 2901 - 51a
Silva MA.Pellegrinet SC.Goodman JM. J. Org. Chem. 2003, 68: 4059 - 51b
Pellegrinet SC.Silva MA.Goodman JM. J. Am. Chem. Soc. 2001, 123: 8832 - 51c
Singleton DA.Kim K.Martinez JP. Tetrahedron Lett. 1993, 34: 3071 - 52
Hilt G.Hess W.Schmidt F. Eur. J. Org. Chem. 2005, 2526 - 53
Hilt G.Lüers S.Smolko KI. Org. Lett. 2005, 7: 251 - 54
Hilt G.Hess W.Harms K. Org. Lett. 2006, 8: 3287 - 55
Hilt G.Galbiati F. Synlett 2005, 829 - 56
Hilt G.Galbiati F.Harms K. Synthesis 2006, 3575 - 57
Wei K.Li W.Koike K.Nikaido T. Org. Lett. 2005, 7: 2833 - Selected references:
- 58a
Smalley TL.Wright MW.Garmon SA.Welker ME.Rheingold AL. Organometallics 1993, 12: 998 - 58b
Tada M.Shimizu T. Bull. Chem. Soc. Jpn. 1992, 65: 1252 - 59a
Chapman JJ.Day CS.Welker ME. Eur. J. Org. Chem. 2001, 2273 - 59b
Chapman JJ.Day CS.Welker ME. Organometallics 2000, 19: 1615 - 60
Pickin KA.Kindy JM.Day CS.Welker ME. J. Organomet. Chem. 2003, 681: 120 - 61
Tucker CJ.Welker ME.Day CS.Wright MW. Organometallics 2004, 23: 2257 - 62
Adams TA.Welker ME.Day CS. J. Org. Chem. 1998, 63: 3683 - 63
Pardigon O.Tenaglia A.Buono G. J. Org. Chem. 1995, 60: 1868 - 64a
Brunner H.Reimer A. Bull. Soc. Chim. Fr. 1997, 134: 307 - 64b
Lautens M.Tam W.Lautens JC.Edwards LG.Crudden CM.Smith AC. J. Am. Chem. Soc. 1995, 117: 6863 - 65a
See ref. 41c.
- 65b
For Snyder’s work, see references 139-144.
- 66
Pardigon O.Tenaglia A.Buono G. J. Mol. Catal. A: Chem. 2003, 196: 157 - 67a
Buschmann H.Scharf HD.Hoffmann N.Esser P. Angew. Chem., Int. Ed. Engl. 1991, 30: 477 ; Angew. Chem. 1991, 103, 480 - 67b
Meyer-Stork MA.Haag D.Scharf HD. J. Chem. Soc., Perkin Trans. 2 1997, 593 - 68a
See ref. 2j.
- 68b
Kotha S.Brahmachary E.Lahiri K. Eur. J. Org. Chem. 2005, 4741 - 68c
Gandon V.Aubert C.Malacria M. Chem. Commun. 2006, 2209 - 68d
Chopade PR.Louie J. Adv. Synth. Catal. 2006, 348: 2307 - 69a
Agenet N.Gandon V.Vollhardt KPC.Malacria M.Aubert C. J. Am. Chem. Soc. 2007, 129: 8860 - 69b
Dierecks R.Eaton BE.Gürtzgen S.Jalisatgi S.Matzger AJ.Radde RH.Vollhardt KPC. J. Am. Chem. Soc. 1998, 120: 8247 - 70
Chouraqui G.Petit M.Aubert C.Malacria M. Org. Lett. 2004, 6: 1519 - 71a
Goswami A.Maier C.-J.Pritzkow H.Siebert W. Eur. J. Inorg. Chem. 2004, 2635 - 71b
Ester C.Maderna A.Pritzkow H.Siebert W. Eur. J. Inorg. Chem. 2000, 1177 - 72
Geny A.Leboeuf D.Rouqui G.Vollhardt KPC.Malacria M.Gandon V.Aubert C. Chem. Eur. J. 2007, 13: 5408 - 73
Goswami A.Maier C.-J.Pritzkow H.Siebert W. J. Organomet. Chem. 2005, 690: 3251 - 74
Sigman MS.Fatland AW.Eaton BE. J. Am. Chem. Soc. 1998, 120: 5130 - 75
Yong L.Butenschön H. Chem. Commun. 2002, 2852 - 76
Lombardo M.Pasi F.Trombini C.Seddon KR.Pitner WR. Green Chem. 2007, 9: 321 - 77a
Hilt G.Hess W.Vogler T.Hengst C. J. Organomet. Chem. 2005, 690: 5170 - 77b
Hilt G.Vogler T.Hess W.Galbiati F. Chem. Commun. 2005, 1474 - 78
Hilt G.Hengst C.Hess W. Eur. J. Org. Chem. 2008, 2293 - 79
Chang H.-T.Jeganmohan M.Cheng C.-H. Chem. Commun. 2005, 4955 - 80
Mamane V.Gref A.Lefloch F.Riant O. J. Organomet. Chem. 2001, 637-639: 84 - 81
Hahn U.Maisonhaute E.Amatore C.Nierengarten C.-F. Angew. Chem. Int. Ed. 2007, 46: 951 ; Angew. Chem. 2007, 119, 969 - 82
Gandon V.Leca D.Aechtner T.Vollhardt KPC.Malacria M.Aubert C. Org. Lett. 2004, 6: 3405 - 83
Saino N.Amemiya F.Tanabe E.Kase K.Okamoto S. Org. Lett. 2006, 8: 1439 - 84
Goswami A.Ito T.Okamoto S. Adv. Synth. Catal. 2007, 349: 2368 - 85a
Doszczak L.Tacke R. Organometallics 2007, 26: 5722 - 85b
Doszczak L.Fey P.Tacke R. Synlett 2007, 753 - 86
Büttner MW.Natscher JB.Burschka C.Tacke R. Organometallics 2007, 26: 4835 - 87
Moser M.Sun X.Hudlicky T. Org. Lett. 2005, 7: 5669 - 88
Kotha S.Brahmachary E. Bioorg. Med. Chem. 2002, 10: 2291 - 89a
Turek P.Kotora M.Tislerova I.Hocek M.Votruba I.Cisarova I. J. Org. Chem. 2004, 69: 9224 - 89b
Turek P.Kotora M.Hocek M.Cisarova I. Tetrahedron Lett. 2003, 44: 785 - 90
Dufkova L.Cisarova I.Štepnička P.Kotora M. Eur. J. Org. Chem. 2003, 2882 - 91
Mohamed AB.Green JR. Chem. Commun. 2003, 2936 - 92
Son SU.Paik S.-J.Lee SI.Chung YK. J. Chem. Soc., Perkin Trans. 1 2000, 141 - 93
Sugihara T.Wakabayashi A.Nagai Y.Takao H.Imagawa H.Nishizawa M. Chem. Commun. 2002, 576 - 94
Slowinski F.Aubert C.Malacria M. Adv. Synth. Catal. 2001, 343: 64 - 95
Saino N.Kogure D.Okamoto S. Org. Lett. 2005, 7: 3065 - 96a
Kalogerakis A.Groth U. Synlett 2003, 1886 - 96b
Kalogerakis A.Groth U. Org. Lett. 2003, 5: 843 - 97
Petit M.Chouraqui G.Phansavath P.Aubert C.Malacria M. Org. Lett. 2002, 4: 1027 - 98a
Mohler DL.Kumaraswamy S.Stanger A.Vollhardt KPC. Synlett 2006, 2981 - 98b
Han S.Bond AD.Disch RL.Holmes D.Schulman JM.Teat SJ.Vollhardt KPC.Whitener GD. Angew. Chem. Int. Ed. 2002, 41: 3223 ; Angew. Chem. 2002, 114, 3357 - 98c
Han S.Anderson DR.Bond AD.Chu HV.Disch RL.Holmes D.Schulman JM.Teat SJ.Vollhardt KPC.Whitener GD. Angew. Chem. Int. Ed. 2002, 41: 3227 ; Angew. Chem. 2002, 114, 3361 - 98d
Dosa PI.Whitener GD.Vollhardt KPC.Bond AD.Teat SJ. Org. Lett. 2002, 4: 2075 - 98e
Bong DT.-Y.Gentric L.Holmes D.Matzger AJ.Scherhag F.Vollhardt KPC. Chem. Commun. 2002, 278 - 99
Gandon V.Agenet N.Vollhardt KPC.Malacria M.Aubert C. J. Am. Chem. Soc. 2006, 128: 8509 - 100
Gandon V.Leboeuf D.Amslinger S.Vollhardt KPC.Malacria M.Aubert C. Angew. Chem. Int. Ed. 2005, 44: 7114 ; Angew. Chem. 2005, 117, 7276 - 101
Hong SH.Kim JW.Choi DS.Chung YK.Lee S.-G. Chem. Commun. 1999, 2099 - 102
Wu M.-S.Rayabarapu DK.Cheng C.-H. Tetrahedron 2004, 60: 10005 - 103
Wu M.-S.Shanmugasundaram M.Cheng C.-H. Chem. Commun. 2003, 718 - 104a
Aubert C.Gandon V.Geny N.Heckrodt TJ.Malacria M.Paredes E.Vollhardt KPC. Chem. Eur. J. 2007, 13: 7466 - 104b
Aubert C.Betschmann P.Eichberg MJ.Gandon V.Heckrodt TJ.Lehmann J.Malacria M.Masjost B.Paredes E.Vollhardt KPC.Whitener GD. Chem. Eur. J. 2007, 13: 7443 - 104c
Pelissier H.Rodriguez J.Vollhardt KPC. Chem. Eur. J. 1999, 5: 3549 - 105
Pérez D.Siesel BA.Malaska MJ.David E.Vollhardt KPC. Synlett 2000, 306 - 106a
Eichberg MJ.Dorta RL.Grotjahn DB.Lamottke K.Schmidt M.Vollhardt KPC. J. Am. Chem. Soc. 2001, 123: 9324 - 106b
Eichberg MJ.Dorta RL.Lamottke K.Vollhardt KPC. Org. Lett. 2000, 2: 2479 - 107
Slowinski F.Aubert C.Malacria M. J. Org. Chem. 2003, 68: 378 - 108
Schelper M.Buisine O.Kozhushkov S.Aubert C.de Meijere A.Malacria M. Eur. J. Org. Chem. 2005, 3000 - 109
Buisine O.Aubert C.Malacria M. Synthesis 2000, 985 - 110
Petit M.Aubert C.Malacria M. Org. Lett. 2004, 6: 3937 - 111a
Dazinger G.Torres-Rodrigues M.Kirchner K.Calhorda MJ.Costa PJ. J. Organomet. Chem. 2006, 691: 4434 - 111b
See ref. 1c
- 112
Heller B.Heller D.Wagler P.Oehme G. J. Mol. Catal. A: Chem. 1998, 136: 219 - 113
Fatland AW.Eaton BE. Org. Lett. 2000, 2: 3131 - 114
Brändli C.Ward TR. J. Comb. Chem. 2000, 2: 42 - 115
Senaiar RS.Young DD.Deiters A. Chem. Commun. 2006, 1313 - 116
Young DD.Deiters A. Angew. Chem. Int. Ed. 2007, 46: 5187 ; Angew. Chem. 2007, 119, 5279 - 117
Kase K.Goswami A.Ohtaki K.Tanabe E.Saino N.Okamoto S. Org. Lett. 2007, 9: 931 - 118
Goswami A.Ohtaki K.Kase K.Ito T.Okamoto S. Adv. Synth. Catal. 2008, 350: 143 - 119
Varela JA.Castedo L.Maestro M.MahÌa J.Saá C. Chem. Eur. J. 2001, 7- 23: 5203 - 120
Varela JA.Castedo L.Saá C. Org. Lett. 1999, 1: 2141 - 121
Bonaga LVR.Zhang H.-C.Maryanoff BE. Chem. Commun. 2004, 2394 - 122a
Maryanoff BE.Zhang H.-C. ARKIVOC 2007, (xii): 7 - 122b
Maryanoff BE. J. Am. Chem. Soc. 2005, 127: 3473 - 122c
Moretto AF.Zhang H.-C.Maryanoff BE. J. Am. Chem. Soc. 2001, 123: 3157 - 123
Gutnov A.Abaev V.Redkin D.Fischer C.Bonrath W.Heller B. Synlett 2005, 1188 - 124
Gutnov A.Heller B.Fischer C.Drexler H.-J.Spannenberg A.Sundermann B.Sundermann C. Angew. Chem. Int. Ed. 2004, 43: 3795 ; Angew. Chem. 2004, 116, 3883 - 125
Zhou Y.Porco A.Snyder JK. Org. Lett. 2007, 9: 393 - 126
Chang H.-T.Jeganmohan M.Cheng C.-H. Org. Lett. 2007, 9: 505 - 127
Groth U.Huhn T.Kesenheimer C.Kalogerakis A. Synlett 2005, 1758 - 128
Míšek J.Teplý F.Stará IG.Tichý M.Šaman D.Císařová I.Vojtíšek P.Starý I. Angew. Chem. Int. Ed. 2008, 47: 3188 ; Angew. Chem. 2008, 120, 3232 - 129
Sehnal P.Krausová Z.Teplý F.Stará IG.Starý I.Rulýšek L.Saman D.Císařová I. J. Org. Chem. 2008, 73: 2074 - 130a
Dzwiniel TL.Etkin N.Stryker JM. J. Am. Chem. Soc. 1999, 121: 10640 - 130b
Etkin N.Dzwiniel TL.Schweibert KE.Stryker JM. J. Am. Chem. Soc. 1998, 120: 9702 - 131
Witherell RD.Ylijoki KEO.Stryker JM. J. Am. Chem. Soc. 2008, 130: 2176 - 132a
Tanino K.Kondo F.Shimizu T.Miyashita M. Org. Lett. 2002, 4: 2217 - 132b
Tanino K.Shimizu T.Miyama M.Kuwajima I. J. Am. Chem. Soc. 2000, 122: 6116 - 133a
Demuner AJ.Barbosa LCA.Pilo-Veloso D. Quim. Nova 1997, 20: 18 - 133b
Mann J. Tetrahedron 1986, 42: 4611 - 133c
Noyori R. Org. React. 1983, 29: 163 - 134
Molander GA.Eastwood PR. J. Org. Chem. 1995, 60: 8382 ; and references cited therein - 135
Patel MM.Green JR. Chem. Commun. 1999, 509 - 136
Lu Y.Green JR. Synlett 2001, 243 - 137a
Achard M.Mosrin M.Tenaglia A.Buono G. J. Org. Chem. 2006, 71: 2907 - 137b
Achard M.Tenaglia A.Buono G. Org. Lett. 2005, 7: 2353 - 138
Toselli N.Martin D.Achard M.Tenaglia A.Bürgi T.Buono G. Adv. Synth. Catal. 2008, 350: 280 - 139a
Ma B.Snyder JK. Organometallics 2002, 21: 4688 - 139b
Chen Y.Kiattansakul R.Ma B.Snyder JK. J. Org. Chem. 2001, 66: 6932 - 139c
Chen Y.Snyder JK. J. Org. Chem. 1998, 63: 2060 - 140
Kiattansakul R.Snyder JK. Tetrahedron Lett. 1999, 40: 1079 - 141
Hours AE.Snyder JK. Tetrahedron Lett. 2006, 47: 675 - 142
Chen Y.Snyder JK. J. Org. Chem. 2001, 66: 6943 - 143
Ma B.Snyder JK. Tetrahedron Lett. 2005, 46: 703 - 144
Ma B.Snyder JK. Org. Lett. 2002, 4: 2731 - 145
Hilt G.Janikowski J. Angew. Chem. Int. Ed. 2008, 47: 5243; Angew. Chem. 2008, 120, 5321 - 146
Pidaparthi RR.Welker ME.Day CS. Organometallics 2006, 25: 974 - 147a
Wang C.-C.Lin P.-S.Cheng C.-H. J. Am. Chem. Soc. 2002, 124: 9696 - 147b
Chang H.-T.Jayanth TT.Wang C.-C.Cheng C.-H. J. Am. Chem. Soc. 2007, 129: 12032 - 148a
See ref. 110
- 148b
Buisine O.Aubert C.Malacria M. Chem. Eur. J. 2001, 7: 3517 - 148c
Llerena D.Aubert C.Malacria M. Tetrahedron Lett. 1996, 37: 7027 - 149
Hilt G.Treutwein J. Angew. Chem. Int. Ed. 2007, 46: 8500 ; Angew. Chem. 2007, 119, 8653 - For alternative transition-metal-catalysed Alder-ene reactions, see:
- 150a
Trost BM.Martinez JA.Kulawiec RJ.Indolese AF. J. Am. Chem. Soc. 1993, 115: 10402 - 150b
Trost BM.Machacek M.Schnaderbeck MJ. Org. Lett. 2000, 2: 1761 - 150c
Trost BM. Acc. Chem. Res. 2002, 35: 695 - 150d
Trost BM.Shen HC.Pinkerton AB. Chem. Eur. J. 2002, 8: 2341 - 150e
Trost BM.Frederiksen MU.Rudd MD. Angew. Chem. Int. Ed. 2005, 44: 6630 ; Angew. Chem. 2005, 117, 6788 - 151
Amatore M.Gosmini C. Angew. Chem. Int. Ed. 2008, 47: 2089 ; Angew. Chem. 2008, 120, 2119 - 152
Wong Y.-C.Jayanth TT.Cheng C.-H. Org. Lett. 2006, 8: 5613 - 153a
Chang K.-J.Rayabarapu DK.Cheng C.-H. J. Org. Chem. 2004, 69: 4781 - 153b
Chang K.-J.Rayabarapu DK.Cheng C.-H. Org. Lett. 2003, 5: 3963 - For an overview of cobalt-catalysed reactions with Grignard reagents, see the following references and the references cited therein:
- 154a
Yorimitsu H.Oshima K. Pure Appl. Chem. 2006, 78: 441 - 154b
Shinokubo H.Oshima K. Eur. J. Org. Chem. 2004, 2081 - 155
Shirakawa E.Sato T.Imazaki Y.Kimura T.Hayashi T. Chem. Commun. 2007, 4513 - 156a
Gaspar B.Carreira EM. Angew. Chem. Int. Ed. 2007, 46: 4519 ; Angew. Chem. 2007, 119, 4603 - For a similar synthesis of azides, see:
- 156b
Gaspar B.Waser J.Carreira EM. Synthesis 2007, 3839 - 157
Oshmiya H.Yorimitsu H.Oshima K. Angew. Chem. Int. Ed. 2005, 44: 2368 ; Angew. Chem. 2005, 117, 2420 - 158 See ref. 41a
- 159
Yong L.Kirleis K.Butenschön H. Adv. Synth. Catal. 2006, 348: 833 - 160a
Hilt G.du Mesnil F.-X.Lüers S. Angew. Chem. Int. Ed. 2001, 40: 387 ; Angew. Chem. 2001, 113, 408 - 160b
Hilt G.Lüers S. Synthesis 2002, 609 - 161
Michiel MP.Müller C.Vogt D. J. Am. Chem. Soc. 2006, 128: 7414 - 162
Gomes P.Gosmini C.Nédélec J.-Y.Périchon J. Tetrahedron Lett. 2000, 41: 3385 - 163
Shukla P.Hsu Y.-C.Cheng C.-H. J. Org. Chem. 2006, 71: 655 - 164
Lombardo M.Gualandi A.Pasi F.Trombini C. Adv. Synth. Catal. 2007, 349: 465 - 165a
Nishikawa T.Yorimitsu H.Oshima K. Synlett 2004, 1573 - 165b
Yasui H.Nishikawa T.Yorimitsu H.Oshima K. Bull. Chem. Soc. Jpn. 2006, 79: 1271 - See, for a similar reaction sequence:
- 165c
Lumby RJR.Joensuu PM.Lam HW. Org. Lett. 2007, 9: 4367 - 166
Shimakoshi H.Ninomiya W.Hisaeda Y. J. Chem. Soc., Dalton Trans. 2001, 1971 - 167
Eisenmann JL.Yamartino RL.Howard JF. J. Org. Chem. 1961, 26: 2102 - 168a
Allmendinger M.Eberhardt R.Luinstra GA.Molnar F.Rieger B. Z. Anorg. Allg. Chem. 2003, 629: 1347 - 168b
Molnar F.Luinstra GA.Allmendinge M.Rieger B. Chem. Eur. J. 2003, 9: 1273 - 168c
Allmendinger M.Zintl M.Eberhardt R.Luinstra GA.Molnar F.Rieger B. J. Organomet. Chem. 2004, 689: 971 - 169
Kim HS.Bae JY.Lee JS.Jeong CI.Choi DK.Kang SO.Cheong M. Appl. Catal. A 2006, 301: 75 - 170
Liu J.Chen J.Xia C. J. Mol. Catal. A: Chem. 2006, 250: 232 - 171
Hinterding K.Jacobsen EN. J. Org. Chem. 1999, 64: 2164 - 172
Goodman SN.Jacobsen EN. Angew. Chem. Int. Ed. 2002, 41: 4703 ; Angew. Chem. 2002, 114, 4897 - 173
Denmark SE.Ahmad M. J. Org. Chem. 2007, 72: 9630 - 174a
Seki Y.Murai S.Yamamoto I.Noboru S. Angew. Chem. Int. Ed. 1977, 16: 789 ; Angew. Chem. 1977, 89, 818 - 174b
Murai S.Toki T.Suzuki S.Sonoda N. J. Am. Chem. Soc. 1984, 106: 6093 - 174c
Murai T.Yasui E.Kato S.Hatayama Y.Suzuki S.Yamasaki Y.Sonoda N.Kurosawa H.Kawasaki Y.Murai S. J. Am. Chem. Soc. 1989, 111: 7938 - 175a
Tsuji Y.Kobayashi M.Okuda F.Watanabe Y. J. Chem. Soc., Chem. Commun. 1989, 1253 - 175b
Watanabe Y.Nishiyama K.Zhang K.Okuda F.Kondo T.Tsuji Y. Bull. Chem. Soc. Jpn. 1994, 67: 879 - 176a
Davoli P.Moretti I.Prati F.Alper H. J. Org. Chem. 1999, 64: 518 - 176b
Lee JT.Thomas PJ.Alper H. J. Org. Chem. 2001, 66: 5424 - 177a
Getzler YDYL.Mahadevan V.Lobkovsky EB.Coates GW. J. Am. Chem. Soc. 2002, 124: 1174 - 177b
Mahadevan V.Getzler YDYL.Coates GW. Angew. Chem. Int. Ed. 2002, 41: 2781 ; Angew. Chem. 2002, 114, 2905 - 178a
Schmidt JAR.Mahadevan V.Getzler YDYL.Coates GW. Org. Lett. 2003, 6: 373 - 178b
Schmidt JAR.Lobkobsky EB.Coates GW. J. Am. Chem. Soc. 2005, 127: 11426 - 179
Rowley JM.Lobkovsky EB.Coates GW. J. Am. Chem. Soc. 2007, 129: 4948 - 180a
Jia L.Ding E.Anderson WR. Chem. Commun. 2001, 1436 - 180b
Jia L.Sun H.Shay JT.Allgeier AM.Hanton SD. J. Am. Chem. Soc. 2002, 124: 7282 - 180c
Liu G.Jia L. J. Am. Chem. Soc. 2004, 126: 14716 - 181
Funk JK.Yennawar H.Sen A. Helv. Chim. Acta 2006, 89: 1687 - 182
Harden JD.Ruppeö JV.Gao G.-Y.Zhang XP. Chem. Commun. 2007, 4644 - 183
Gandon V.Aubert C.Malacria M.Vollhardt KPC. Chem. Commun. 2008, 1599 - 184
Lee M.-Y.Chen Y.Zhang XP. Organometallics 2003, 23: 4905 - 185
Wang C.-C.Lin P.-S.Cheng C.-H. Tetrahedron Lett. 2004, 45: 6203 - 186
Hutson GE.Dave AH.Rawal VH. Org. Lett. 2007, 9: 3869 - 187
Gelman F.Avnir D.Schumann H.Blum J. J. Mol. Catal. A: Chem. 2001, 171: 191 - 188
Bolig AD.Brookhardt M. J. Am. Chem. Soc. 2007, 129: 14544 - 189a
Fernández I.Pedro JR.Roselló AL.Ruiz R.Castro I.Ottenwaelder X.Journaux Y. Eur. J. Org. Chem. 2001, 1235 - 189b
Blay G.Cardona GL.Fernández I.Pedro JR. Synthesis 2007, 3329 - 190
Yanagitas H.Kodama K.Kanemasa S. Tetrahedron Lett. 2006, 47: 9353 - 191
Belokon YN.Petrosyan AA.Maleev VI.Savel’eva TF.Grachev AV.Ikonnikov NS.Sagiyan AS. Russ. Chem. Bull. 2002, 51: 2086 - 192
Agenet N.Mirebeau J.-H.Petit M.Thouvenot R.Gandon V.Malacria M.Aubert C. Organometallics 2007, 26: 819