Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Download PDF
Synlett 2003(2): 0156-0165
DOI: 10.1055/s-2003-36775
DOI: 10.1055/s-2003-36775
ACCOUNT
© Georg Thieme Verlag Stuttgart · New YorkCarbon-Heteroatom Bond-Forming Reactions Mediated by Cerium(IV) Ammonium Nitrate:An Overview
Further Information
Received
10 July 2002
Publication Date:
22 January 2003 (online)
Publication History
Publication Date:
22 January 2003 (online)
Abstract
As a powerful one-electron oxidant, cerium(IV) ammonium nitrate (CAN) is useful for a variety of oxidative transformations including carbon-carbon bond formation. Recent work has also demonstrated the usefulness of CAN in carbon-heteroatom bond-forming reactions. Particularly noteworthy is the effectiveness of CAN in building C-N, C-S, C-Se, C-Br, and C-I bonds. This account is aimed at creating awareness among organic chemists about such reactions with potential application in the synthesis of a variety of building blocks.
1 Introduction
2 Carbon-Carbon Bond-Forming Reactions Mediated by CAN: A Brief Outline
3 Carbon-Heteroatom Bond-Forming Reactions Mediated by CAN
3.1 Carbon-Nitrogen Bond Formation
3.2 Carbon-Sulfur Bond Formation
3.3 Carbon-Selenium Bond Formation
3.4 Carbon-Halogen Bond Formation
4 Conclusion
Key words
cerium(IV) ammonium nitrate - radical reactions - bond-forming reactions - heteroatoms - oxidations
- 1a
Gomberg M. J. Am. Chem. Soc. 1900, 22: 757 - 1b
Gomberg M. Berichte 1900, 33: 3150 - 2a
Hey DH.Waters WA. Chem. Rev. 1937, 21: 169 - 2b
Kharasch MS.Margolis ET.Mayo FR. J. Org. Chem. 1937, 2: 393 - 2c
Mayo FR.Lewis FM. J. Am. Chem. Soc. 1944, 66: 1594 - 3a
Stork G.Baine NH. Tetrahedron Lett. 1985, 26: 5927 - 3b
Stork G.Sher PM. J. Am. Chem. Soc. 1983, 105: 6765 ; and references cited therein - 3c
Stork G. Selectivity-A Goal for Synthetic EfficiencyBartman W.Trost BM. Verlag Chemie; Weinheim: 1981. p.281 - 4
Julia M. Pure Appl. Chem. 1974, 40: 553 - 5a
Beckwith ALJ. Chem. Soc. Rev. 1993, 143 - 5b
Beckwith ALJ. Tetrahedron 1981, 37: 3073 - 6
Giese B. Radicals in Organic Synthesis, Formation of Carbon-Carbon Bonds Pergamon; Oxford: 1986.Reference Ris Wihthout Link - 7
Chatgilialoglu C.Ingold KU.Scaiano JC. J. Am. Chem. Soc. 1981, 103: 7739 ; and references cited therein. - 8
Curran DP. Comprehensive Organic Synthesis Vol. 4:Trost BM.Fleming I. Pergamon; New York: 1991. p.715Reference Ris Wihthout Link - 9
Pattenden G.Smithies AJ.Tapolczy D.Walter DS. J. Chem. Soc., Perkin Trans. 1 1996, 7 ; and references cited therein. - 10a
De Klein WJ. Organic Synthesis by Oxidation with Metal CompoundsMijs WJ.de Jonge CRH. Plenum; New York: 1986. p.261Reference Ris Wihthout Link - 10b
Iqbal J.Bhatia B.Nayyar NK. Chem. Rev. 1994, 94: 519Reference Ris Wihthout Link - 10c
Molander GA. Chem. Rev. 1992, 92: 29Reference Ris Wihthout Link - 11
Ho TL. Synthesis 1973, 347 - 12a
Heiba EI.Dessau RM. J. Am. Chem. Soc. 1971, 93: 524 - 12b
Heiba EI.Dessau RM. J. Am. Chem. Soc. 1971, 93: 995 - 12c
Heiba EI.Dessau RM. J. Am. Chem. Soc. 1972, 94: 2888 - 12d
Heiba EI.Dessau RM.Rodewald PG. J. Am. Chem. Soc. 1974, 96: 7977 - 13 For reviews on CAN-mediated reactions,
see:
Imamoto T. Lanthanide Reagents in Organic Synthesis Academic Press; London: 1994. p.119Reference Ris Wihthout Link - 14
Nair V.Mathew J.Radhakrishnan KV. J. Chem. Soc., Perkin Trans. 1 1995, 1487 ; and references cited therein - 15
Nair V.Mathew J.Prabhakaran J. Chem. Soc. Rev. 1997, 127 - 16
Baciocchi E.Ruzziconi R. Synth. Commun. 1988, 18: 1841 - 17
Baciocchi E.Ruzziconi R. J. Org. Chem. 1986, 51: 1645 - 18
Baciocchi E.Ruzziconi R. Gazz. Chim. Ital. 1986, 116: 671 - 19
Linker T.Hartmann K.Sommermann T.Scheutzow D.Ruckdeschel E. Angew. Chem., Int. Ed. Engl. 1996, 35: 1730 - 20
Hwu JR.Chen CN.Shiao S.-S. J. Org. Chem. 1995, 60: 856 - 21
Kurz ME.Ngoviwatchai P. J. Org. Chem. 1981, 46: 4672 - 22
Baciocchi E.Ruzziconi R.Airra DD. Tetrahedron Lett. 1986, 27: 2763 - 23
Kurz ME.Baru V.Nguyen PN. J. Org. Chem. 1984, 49: 1603 - 24
Nair V.Mathew J. J. Chem. Soc., Perkin Trans. 1 1995, 187 - 25
Nair V.Nair LG.Balagopal L.Mathew J. Indian. J. Chem., Sect. B 2000, 39: 352 - 26
Nair V.Mathew J.Alexander S. Synth. Commun. 1995, 25: 3981 - 27a
Nair V.Mathew J. J. Chem. Soc., Perkin Trans. 1 1995, 1881 - 27b
Nair V.Mathew J.Nair LG. Synth. Commun. 1997, 27: 3064 - 28a
Nair V.Mathew J.Kanakamma PP.Panicker SB.Sheeba V.Zeena S.Eigendorf GK. Tetrahedron Lett. 1997, 38: 2191 - 28b
Nair V.Sheeba V.Panicker SB.George TG.Rajan R.Balagopal L.Vairamani M.Prabhakar S. Tetrahedron 2000, 56: 2461 - 30
Snider BB.Kwon T. J. Org. Chem. 1990, 55: 4786 - 31a
Durand A.-C.Dumez E.Rodriguez J.Dulcere J.-P. Chem. Commun.(Cambridge) 1999, 2437 - 31b
Durand A.-C.Rodriguez J.Dulcere J.-P. Synlett 2000, 731 - 32
Kim HJ.Yoon UC.Jung Y.Park S.Cederstorm EM.Mariano PS. J. Org. Chem. 1998, 63: 860 - 33
Attenni B.Cerreti A.Annibale AD.Resta S.Troglo C. Tetrahedron 1998, 54: 12029 - 34
Nair V.Balagopal L.Sheeba V.Panicker SB.Rath NP. Chem. Commun. 2001, 1682 - 35
Trahanovsky WS.Robbins MD. J. Am. Chem. Soc. 1971, 93: 5256 - 36
Hansen RS.Trahanovsky WS. J. Org. Chem. 1974, 39: 570 - 37
Lemieux RU.Ratcliffe RM. Can J. Chem. 1979, 57: 1244 - 38a
Bertozzi CR.Bednarski MD. Tetrahedron Lett. 1992, 33: 3109 - 38b
Berlin WK.Zhang W.-S.Shen TY. Tetrahedron 1991, 47: 1 - 39
Magnus P.Barth L. Tetrahedron Lett. 1992, 33: 2777 - 40
Auberson Y.Vogel P. Tetrahedron 1990, 45: 7019 - 41
Clive DLJ.Etkin N. Tetrahedron Lett. 1994, 35: 2459 - 42
Chavan SP.Subbarao YT. Tetrahedron Lett. 1999, 40: 5073 - 43
Nair V.Nair LG.George TG.Augustine A. Tetrahedron 2000, 56: 7607 - 44
Nair V.George TG. Tetrahedron Lett. 2000, 41: 3199 - 45
Iranpoor N.Kazemi F. Synth. Commun. 1999, 29: 561 - 46a
Hwu JR.Chen KL.Ananthan S. J. Chem. Soc., Chem. Commun. 1994, 1425 - 46b
Hwu JR.Chen KL.Ananthan S.Patel HV. Organometallics 1996, 15: 499 - 47
Reddy MVR.Mehrotra B.Vankar YD. Tetrahedron Lett. 1995, 36: 4861 - 48
Smith CC.Jacyno JM.Zeiter KK.Prakanzky P.Paxson C.Pekelnicky P.Harwood JS.Hunter AD.Lucarelli VG.Lufaso MW.Cutler HG. Tetrahedron Lett. 1998, 39: 6617 - 49
Chawla HM.Mittal RS. Synthesis 1985, 70 - 50a
Chawla HM.Mittal RS. Indian J. Chem., Sect. B 1983, 22: 753 - 50b
Chawla HM.Mittal RS. Indian J. Chem., Sect. B 1983, 22: 751 - 51
Mellor JM.Parkes R.Millar RW. Tetrahedron Lett. 1997, 38: 8739 - 52a
Narasaka K.Mochizuki T.Hayakawa S. Chem. Lett. 1994, 1705 - 52b
Mochizuki T.Hayakawa S.Narasaka K. Bull. Chem. Soc. Jpn. 1996, 69: 2317 - 53 Nair, V.; Augustine, A., unpublished
results
Reference Ris Wihthout Link
- 54
Nair V.Augustine A.George TG.Nair LG. Tetrahedron Lett. 2001, 42: 6763 - 55
Nair V.Nair LG. Tetrahedron Lett. 1998, 39: 4585 - 56
Nair V.George TG.Nair LG.Panicker SB. Tetrahedron Lett. 1999, 40: 1105 - 57
Nair V.George TG.Augustine A.Nair LG. Res. Chem. Intermed. 2000, 26: 923 - 58
Bosman C.Annibale AD.Resta S.Trogolo C. Tetrahedron Lett. 1994, 35: 6525 - 60
Sugiyama T. Bull. Chem. Soc. Jpn. 1981, 54: 2847 - 61
Horiuchi CA.Kiji S. Chem. Lett. 1988, 31 - 62
Horiuchi CA.Takahashi E. Bull. Chem. Soc. Jpn. 1994, 67: 271 - 63
Horiuchi CA.Ochiai K.Fukunishi H. Chem. Lett. 1994, 185 - 64
Horiuchi CA.Nishio Y.Gong D.Fujisaki T.Kiji S. Chem. Lett. 1991, 607 - 65
Horiuchi CA.Hosokawa H.Kanamori M.Muramastu Y.Ochiai K.Takahashi E. Chem. Lett. 1995, 13 - 66
Horiuchi CA.Ikeda A.Kanamori M.Hosokawa H.Sugiyama T.Takahashi T. J. Chem. Res., Synop. 1997, 60 - 67
Asakura J.Robins MJ. J. Org. Chem. 1990, 55: 4928 - 68
Asakura J.Robins MJ. Tetrahedron Lett. 1998, 29: 2855 - 69
Rodriguez-Franko MI.Dorronsoro I.Higueras AIH.Antequera G. Tetrahedron Lett. 2001, 42: 863 - 70
Roush WR.Narayan S.Bennett CE.Briner K. Org. Lett. 1999, 1: 895 - 71
Baciocchi E.Crescenzi M. Tetrahedron 1988, 44: 6525 - 72
Roy SC.Guin C.Rana KK.Maiti G. Synlett 2001, 226 - 73
Nair V.Panicker SB.Augustine A.George TG.Thomas S. Tetrahedron 2001, 57: 7417 - 74
Panicker SB. PhD Thesis University of Kerala; India: 2000. p.76Reference Ris Wihthout Link - 75
Nair V.George TG.Sheeba V.Augustine A.Balagopal L.Nair LG. Synlett 2000, 1597 - 76
George TG. PhD Thesis Cochin University of Science and Technology; India: 2000. p.150Reference Ris Wihthout Link
References
Nair, V.; Rajan, R.; Rath, N. P. Org. Lett. 2002, accepted.
59Nair, V.; Augustine, A.; George, T. G. Eur. J. Org. Chem. 2002, accepted.