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Synlett 2011(17): 2443-2458  
DOI: 10.1055/s-0030-1260321
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Design of New ‘DalPhos’ P,N-Ligands: Applications in Transition-Metal Catalysis

Rylan J. Lundgren, Kevin D. Hesp, Mark Stradiotto*
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4J3, Canada
Fax: +1(902)4941310; e-Mail: mark.stradiotto@dal.ca;
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Publication History

Received 1 June 2011
Publication Date:
19 September 2011 (online)

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Abstract

This Account documents our recent progress toward the application of new P,N-ligands in transition-metal catalysis, including Ir-catalyzed ketone transfer hydrogenation, Pd-catalyzed cross-coupling of N-H containing substrates as well as acetone with aryl halides, and Au-catalyzed hydroamination of alkynes with dialkyl­amines.

1 Introduction

2 Ketone Transfer Hydrogenation

3 Pd-Catalyzed C-N Cross-Coupling and Acetone α-Arylation

3.1 Development of a Highly Versatile Catalyst System

3.2 Ammonia Monoarylation

3.3 Hydrazine Monoarylation

3.4 Acetone Monoarylation

4 Au-Catalyzed Hydroamination of Dialkylamines and Alkynes

5 Summary and Conclusions

Key words

cross-coupling - homogeneous catalysis - hydrogen transfer - palladium - amines

    References and Notes

  • 1a Stradiotto M. Cipot J. McDonald R. J. Am. Chem. Soc.  2003,  125:  5618 
    Search in Google Scholar
  • 1b Cipot J. Wechsler D. Stradiotto M. McDonald R. Ferguson MJ. Organometallics  2003,  22:  5185 
    Search in Google Scholar
  • 1c Cipot J. McDonald R. Stradiotto M. Chem. Commun.  2005,  4932 
  • 1d Rankin MA. McDonald R. Ferguson MJ. Stradiotto M. Angew. Chem. Int. Ed.  2005,  44:  3603 
    Search in Google Scholar
  • 1e Rankin MA. McDonald R. Ferguson MJ. Stradiotto M. Organometallics  2005,  24:  4981 
    Search in Google Scholar
  • 1f Cipot J. Vogels CM. McDonald R. Westcott SA. Stradiotto M. Organometallics  2006,  25:  5965 
    Search in Google Scholar
  • 1g Wile BM. Burford RJ. McDonald R. Ferguson MJ. Stradiotto M. Organometallics  2006,  25:  1028 
    Search in Google Scholar
  • 1h Cipot J. McDonald R. Ferguson MJ. Schatte G. Stradiotto M. Organometallics  2007,  26:  594 
    Search in Google Scholar
  • 1i Rankin MA. Schatte G. McDonald R. Stradiotto M. J. Am. Chem. Soc.  2007,  129:  6390 
    Search in Google Scholar
  • 1j Lundgren RJ. Rankin MA. McDonald R. Stradiotto M. Organometallics  2008,  27:  254 
    Search in Google Scholar
  • 1k Stradiotto M. Hesp KD. Lundgren RJ. Angew. Chem. Int. Ed.  2010,  49:  494 
    Search in Google Scholar
  • 2a Noyori R. Hashiguchi S. Acc. Chem. Res.  1997,  30:  97 
    Search in Google Scholar
  • 2b Clapham SE. Hadzovic A. Morris RH. Coord. Chem. Rev.  2004,  248:  2201 
    Search in Google Scholar
  • 2c Gladiali S. Alberico E. Chem. Soc. Rev.  2006,  35:  226 
    Search in Google Scholar
  • 2d Samec JSM. Bäckvall JE. Andersson PG. Brandt P. Chem. Soc. Rev.  2006,  35:  237 
    Search in Google Scholar
  • 2e Ikariya T. Blacker AJ. Acc. Chem. Res.  2007,  40:  1300 
    Search in Google Scholar
  • 3a Hashiguchi S. Fujii A. Takehara J. Ikariya T. Noyori R. J. Am. Chem. Soc.  1995,  117:  7562 
    Search in Google Scholar
  • 3b Takehara J. Hashiguchi S. Fujii A. Inoue S. Ikariya T. Noyori R. Chem. Commun.  1996,  233 
  • 3c Uematsu N. Fujii A. Hashiguchi S. Ikariya T. Noyori R. J. Am. Chem. Soc.  1996,  118:  4916 
    Search in Google Scholar
  • 3d Haack K.-J. Hashiguchi S. Fujii A. Ikariya T. Noyori R. Angew. Chem., Int. Ed. Engl.  1997,  36:  285 
    Search in Google Scholar
  • 3e Matsumura K. Hashiguchi S. Ikariya T. Noyori R. J. Am. Chem. Soc.  1997,  119:  8738 
    Search in Google Scholar
  • 4a Yamakawa M. Ito H. Noyori R. J. Am. Chem. Soc.  2000,  122:  1466 
    Search in Google Scholar
  • 4b Noyori R. Yamakawa M. Hashiguchi S. J. Org. Chem.  2001,  66:  7931 
    Search in Google Scholar
  • 5a Mikhailine A. Lough AJ. Morris RH. J. Am. Chem. Soc.  2009,  131:  1394 
    Search in Google Scholar
  • 5b Zhou SL. Fleischer S. Junge K. Das S. Addis D. Beller M. Angew. Chem. Int. Ed.  2010,  49:  8121 
    Search in Google Scholar
  • 5c Wang C. Pettman A. Basca J. Xiao JL. Angew. Chem. Int. Ed.  2010,  49:  7548 
    Search in Google Scholar
  • 5d Irrgang T. Friedrich D. Kempe R. Angew. Chem. Int. Ed.  2011,  50:  2183 
    Search in Google Scholar
  • 5e Baratta W. Ballico M. Chelucci G. Siega K. Rigo P. Angew. Chem. Int. Ed.  2008,  47:  4362 
    Search in Google Scholar
  • 5f Zweifel T. Naubron JV. Büttner T. Ott T. Grützmacher H. Angew. Chem. Int. Ed.  2008,  47:  3245 
    Search in Google Scholar
  • 6 Lundgren RJ. Rankin MA. McDonald R. Schatte G. Stradiotto M. Angew. Chem. Int. Ed.  2007,  46:  4732 
    CrossrefSearch in Google Scholar
  • 7a Dani P. Karlen T. Gossage RA. Gladiali S. van Koten G. Angew. Chem. Int. Ed.  2000,  39:  743 
    Search in Google Scholar
  • 7b Braunstein P. Fryzuk MD. Naud F. Rettig SJ.
    J. Chem. Soc., Dalton Trans.  1999,  589 
  • 7c Yang H. Alvarez-Gressier M. Lugan N. Mathieu R. Organometallics  1997,  16:  1401 
    Search in Google Scholar
  • 7d Baratta W. Chelucci G. Gladiali S. Siega K. Toniutti M. Zanette M. Zangrando E. Rigo P. Angew. Chem. Int. Ed.  2005,  44:  6214 
    Search in Google Scholar
  • 7e Baratta W. Da Ros P. Del Zotto A. Sechi A. Zangrando E. Rigo P. Angew. Chem. Int. Ed.  2004,  43:  3584 
    Search in Google Scholar
  • 8 Nolan SP. Belderrain TR. Grubbs RH. Organometallics  1997,  16:  5569 
    CrossrefSearch in Google Scholar
  • 9a Gunanathan C. Ben-David Y. Milstein D. Science  2007,  317:  790 
    Search in Google Scholar
  • 9b Gunanathan C. Milstein D. Angew. Chem. Int. Ed.  2008,  47:  8661 
    Search in Google Scholar
  • 9c Gnanaprakasam B. Zhang J. Milstein D. Angew. Chem. Int. Ed.  2010,  49:  1468 
    Search in Google Scholar
  • 10 Lundgren RJ. Stradiotto M. Chem. Eur. J.  2008,  14:  10388 
    CrossrefSearch in Google Scholar
  • 11a Clarke ZE. Maragh PT. Dasgupta TP. Gusev DG. Lough AJ. Abdur-Rashid K. Organometallics  2006,  25:  4113 
    Search in Google Scholar
  • 11b Albrecht M. Miecznikowski JR. Samuel A. Faller JW. Crabtree RH. Organometallics  2002,  21:  3596 
    Search in Google Scholar
  • 12a Hartwig JF. Acc. Chem. Res.  2008,  41:  1534 
    Search in Google Scholar
  • 12b Wolfe JP. Wagaw S. Marcoux JF. Buchwald SL. Acc. Chem. Res.  1998,  31:  805 
    Search in Google Scholar
  • 12c Muci AR. Buchwald SL. In Cross-Coupling Reactions   Vol. 219:  Springer; Berlin: 2002.  p.131 
    Search in Google Scholar
  • 12d Surry DS. Buchwald SL. Angew. Chem. Int. Ed.  2008,  47:  6338 
    Search in Google Scholar
  • 13 Monnier F. Taillefer M. Angew. Chem. Int. Ed.  2009,  48:  6954 
    Search in Google Scholar
  • 14a Schlummer B. Scholz U. Adv. Synth. Catal.  2004,  346:  1599 
    Search in Google Scholar
  • 14b Buchwald SL. Mauger C. Mignani G. Scholz U. Adv. Synth. Catal.  2006,  348:  23 
    Search in Google Scholar
  • 14c Torborg C. Beller M. Adv. Synth. Catal.  2009,  351:  3027 
    Search in Google Scholar
  • 15a Marion N. Nolan SP. Acc. Chem. Res.  2008,  41:  1440 
    Search in Google Scholar
  • 15b Surry DS. Buchwald SL. Chem. Sci.  2011,  2:  27 
    Search in Google Scholar
  • 16a Harkal S. Rataboul F. Zapf A. Fuhrmann C. Riermeier T. Monsees A. Beller M. Adv. Synth. Catal.  2004,  346:  1742 
    Search in Google Scholar
  • 16b Rataboul F. Zapf A. Jackstell R. Harkal S. Riermeier T. Monsees A. Dingerdissen U. Beller M. Chem. Eur. J.  2004,  10:  2983 
    Search in Google Scholar
  • 16c Zapf A. Jackstell R. Rataboul F. Riermeier T. Monsees A. Fuhrmann C. Shaikh N. Dingerdissen U. Beller M. Chem. Commun.  2004,  38 
  • 16d Harkal S. Kumar K. Michalik D. Zapf A. Jackstell R. Rataboul F. Riermeier T. Monsees A. Beller M. Tetrahedron Lett.  2005,  46:  3237 
    Search in Google Scholar
  • 16e Schwarz N. Tillack A. Alex K. Sayyed IA. Jackstell R. Beller M. Tetrahedron Lett.  2007,  48:  2897 
    Search in Google Scholar
  • 16f Hu TJ. Schulz T. Torborg C. Chen XR. Wang J. Beller M. Huang J. Chem. Commun.  2009,  7330 
  • 16g Schulz T. Torborg C. Enthaler S. Schäffner B. Dumrath A. Spannenberg A. Neumann H. Börner A. Beller M. Chem. Eur. J.  2009,  15:  4528 
    Search in Google Scholar
  • 16h Schulz T. Torborg C. Schäffner B. Huang J. Zapf A. Kadyrov R. Börner A. Beller M. Angew. Chem. Int. Ed.  2009,  48:  918 
    Search in Google Scholar
  • 16i Sergeev AG. Schulz T. Torborg C. Spannenberg A. Neumann H. Beller M. Angew. Chem. Int. Ed.  2009,  48:  7595 
    Search in Google Scholar
  • 16j Torborg C. Huang J. Schulz T. Schäffner B. Zapf A. Spannenberg A. Börner A. Beller M. Chem. Eur. J.  2009,  15:  1329 
    Search in Google Scholar
  • 16k Gowrisankar S. Sergeev AG. Anbarasan P. Spannenberg A. Neumann H. Beller M. J. Am. Chem. Soc.  2010,  132:  11592 
    Search in Google Scholar
  • 17a To SC. Kwong FY. Chem. Commun.  2011,  47:  5079 
    Search in Google Scholar
  • 17b So CM. Lau CP. Kwong FY. Chem. Eur. J.  2011,  17:  761 
    Search in Google Scholar
  • 17c Yeung PY. So CM. Lau CP. Kwong FY. Angew. Chem. Int. Ed.  2010,  49:  8918 
    Search in Google Scholar
  • 17d Chow WK. So CM. Lau CP. Kwong FY. J. Org. Chem.  2010,  75:  5109 
    Search in Google Scholar
  • 17e So CM. Lee HW. Lau CP. Kwong FY. Org. Lett.  2009,  11:  317 
    Search in Google Scholar
  • 17f So CM. Lau CP. Kwong FY. Angew. Chem. Int. Ed.  2008,  47:  8059 
    Search in Google Scholar
  • 17g So CM. Lau CP. Chan ASC. Kwong FY. J. Org. Chem.  2008,  73:  7731 
    Search in Google Scholar
  • 18a Singer RA. Caron S. McDermott RE. Arpin P. Do NM. Synthesis  2003,  1727 
  • 18b Singer RA. Tom NJ. Frost HN. Simon WM. Tetrahedron Lett.  2004,  45:  4715 
    Search in Google Scholar
  • 18c Singer RA. Dore ML. Sieser JE. Berliner MA. Tetrahedron Lett.  2006,  47:  3727 
    Search in Google Scholar
  • 18d Withbroe GJ. Singer RA. Sieser JE. Org. Process Res. Dev.  2008,  12:  480 
    Search in Google Scholar
  • 18e Urgaonkar S. Nagarajan M. Verkade JG. J. Org. Chem.  2003,  68:  452 
    Search in Google Scholar
  • 18f Urgaonkar S. Verkade JG. J. Org. Chem.  2004,  69:  9135 
    Search in Google Scholar
  • 18g Reddy CV. Kingston JV. Verkade JG. J. Org. Chem.  2008,  73:  3047 
    Search in Google Scholar
  • 18h Bei XH. Uno T. Norris J. Turner HW. Weinberg WH. Guram AS. Petersen JL. Organometallics  1999,  18:  1840 
    Search in Google Scholar
  • 18i Guram AS. King AO. Allen JG. Wang XH. Schenkel LB. Chan J. Bunel EE. Faul MM. Larsen RD. Martinelli MJ. Reider PJ. Org. Lett.  2006,  8:  1787 
    Search in Google Scholar
  • 18j Guram AS. Wang X. Bunel EE. Faul MM. Larsen RD. Martinelli MJ. J. Org. Chem.  2007,  72:  5104 
    Search in Google Scholar
  • 18k Dai Q. Gao WZ. Liu D. Kapes LM. Zhang XM. J. Org. Chem.  2006,  71:  3928 
    Search in Google Scholar
  • 18l Scrivanti A. Bertoldini M. Matteoli U. Antonaroli S. Crociani B. Tetrahedron  2009,  65:  7611 
    Search in Google Scholar
  • 18m Guo MP. Jian FF. He R. Tetrahedron Lett.  2006,  47:  2033 
    Search in Google Scholar
  • 18n Porzelle A. Woodrow MD. Tomkinson NCO. Org. Lett.  2009,  11:  233 
    Search in Google Scholar
  • 18o Kotecki BJ. Fernando DP. Haight AR. Lukin KA. Org. Lett.  2009,  11:  947 
    Search in Google Scholar
  • 19 Murata M. Buchwald SL. Tetrahedron  2004,  60:  7397 
    CrossrefSearch in Google Scholar
  • 20 Lundgren RJ. Sappong-Kumankumah A. Stradiotto M. Chem. Eur. J.  2010,  16:  1983 
    CrossrefPubMedSearch in Google Scholar
  • 21 Goerlich JR. Schmutzler R. Phosphorus, Sulfur Silicon Relat. Elem.  1995,  102:  211 
    CrossrefSearch in Google Scholar
  • 22a Maiti D. Fors BP. Henderson JL. Nakamura Y. Buchwald SL. Chem. Sci.  2011,  2:  57 
    Search in Google Scholar
  • 22b Fors BP. Buchwald SL. J. Am. Chem. Soc.  2010,  132:  15914 
    Search in Google Scholar
  • 23a Surry DS. Buchwald SL. J. Am. Chem. Soc.  2007,  129:  10354 
    Search in Google Scholar
  • 23b Vo GD. Hartwig JF. J. Am. Chem. Soc.  2009,  131:  11049 
    Search in Google Scholar
  • 23c Aubin Y. Fischmeister C. Thomas CM. Renaud JL. Chem. Soc. Rev.  2010,  39:  4130 
    Search in Google Scholar
  • 23d Klinkenberg JL. Hartwig JF. Angew. Chem. Int. Ed.  2011,  50:  86 
    Search in Google Scholar
  • 23e van der Vlugt JI. Chem. Soc. Rev.  2010,  39:  2302 
    Search in Google Scholar
  • 24 Lundgren RJ. Peters BD. Alsabeh PG. Stradiotto M. Angew. Chem. Int. Ed.  2010,  49:  4071 
    CrossrefSearch in Google Scholar
  • 25 Klinkenberg JL. Hartwig JF. J. Am. Chem. Soc.  2010,  132:  11830 
    CrossrefSearch in Google Scholar
  • 26a Sundberg RJ. Indoles   Academic Press; San Diego: 1999. 
  • 26b Katritzky AR. Pozharskii AF. Handbook of Heterocyclic Chemistry   2nd ed.:  Pergamon; Oxford: 2000. 
    Search in Google Scholar
  • 27a Roden BA. In Encyclopedia of Reagents for Organic Synthesis   Paquette LA. John Wiley and Sons; Chester/West Sussex: 2001. 
  • 27b Cellier PP. Spindler JF. Taillefer M. Cristau HJ. Tetrahedron Lett.  2003,  44:  7191 
    Search in Google Scholar
  • 28a Lee KS. Lim YK. Cho CG. Tetrahedron Lett.  2002,  43:  7463 
    Search in Google Scholar
  • 28b Ellames GJ. Gibson JS. Herbert JM. McNeill AH. Tetrahedron  2001,  57:  9487 
    Search in Google Scholar
  • 28c Alonso F. Radivoy G. Yus M. Tetrahedron  2000,  56:  8673 
    Search in Google Scholar
  • 29a Halland N. Nazaré M. R’Kyek O. Alonso J. Urmann M. Lindenschmidt A. Angew. Chem. Int. Ed.  2009,  48:  6879 
    Search in Google Scholar
  • 29b Viña D. del Olmo E. López-Pérez JL. San Feliciano A. Org. Lett.  2007,  9:  525 
    Search in Google Scholar
  • 29c Cho CS. Patel DB. Tetrahedron  2006,  62:  6388 
    Search in Google Scholar
  • 29d Cacchi S. Fabrizi G. Goggiamani A. Sgalla S. Adv. Synth. Catal.  2007,  349:  453 
    Search in Google Scholar
  • 29e Liu X. Barry M. Tsou HR. Tetrahedron Lett.  2007,  48:  8409 
    Search in Google Scholar
  • 29f Cacchi S. Fabrizi G. Goggiamani A. Licandro E. Maiorana S. Perdicchia D. Org. Lett.  2005,  7:  1497 
    Search in Google Scholar
  • 29g Song JJ. Yee NK. Org. Lett.  2000,  2:  519 
    Search in Google Scholar
  • 29h Rao HH. Jin Y. Fu H. Jiang YY. Zhao YF. Chem. Eur. J.  2006,  12:  3636 
    Search in Google Scholar
  • 30a Mauger C. Mignani G. Adv. Synth. Catal.  2005,  347:  773 
    Search in Google Scholar
  • 30b Lebedev AY. Khartulyari AS. Voskoboynikov AZ. J. Org. Chem.  2005,  70:  596 
    Search in Google Scholar
  • 30c Cho CS. Lim DK. Heo NH. Kim TJ. Shim SC. Chem. Commun.  2004,  104 
  • 30d Arterburn JB. Rao KV. Ramdas R. Dible BR. Org. Lett.  2001,  3:  1351 
    Search in Google Scholar
  • 30e Wagaw S. Yang BH. Buchwald SL. J. Am. Chem. Soc.  1999,  121:  10251 
    Search in Google Scholar
  • 30f Wagaw S. Yang BH. Buchwald SL. J. Am. Chem. Soc.  1998,  120:  6621 
    Search in Google Scholar
  • 30g Klapars A. Antilla JC. Huang XH. Buchwald SL. J. Am. Chem. Soc.  2001,  123:  7727 
    Search in Google Scholar
  • 30h Pabba C. Wang HJ. Mulligan SR. Chen ZJ. Stark TM. Gregg BT. Tetrahedron Lett.  2005,  46:  7553 
    Search in Google Scholar
  • 30i Inamoto K. Katsuno M. Yoshino T. Suzuki I. Hiroya K. Sakamoto T. Chem. Lett.  2004,  33:  1026 
    Search in Google Scholar
  • 31a Reichelt A. Falsey JR. Rzasa RM. Thiel OR. Achmatowicz MM. Larsen RD. Zhang DW. Org. Lett.  2010,  12:  792 
    Search in Google Scholar
  • 31b Barluenga J. Moriel P. Aznar F. Valdés C. Org. Lett.  2007,  9:  275 
    Search in Google Scholar
  • 31c Lim YK. Jung JW. Lee H. Cho CG. J. Org. Chem.  2004,  69:  5778 
    Search in Google Scholar
  • 31d Lim YK. Lee KS. Cho CG. Org. Lett.  2003,  5:  979 
    Search in Google Scholar
  • 31e Wang Z. Skerlj RT. Bridger GJ. Tetrahedron Lett.  1999,  40:  3543 
    Search in Google Scholar
  • 31f Rivero MR. Buchwald SL. Org. Lett.  2007,  9:  973 
    Search in Google Scholar
  • 31g Loog O. Mäeorg U. Synlett  2004,  2537 
  • 31h Wolter M. Klapars A. Buchwald SL. Org. Lett.  2001,  3:  3803 
    Search in Google Scholar
  • 32 Lundgren RJ. Stradiotto M. Angew. Chem. Int. Ed.  2010,  49:  8686 
    CrossrefSearch in Google Scholar
  • 33 Schmidt A. Beutler A. Snovvdovych B. Eur. J. Org. Chem.  2008,  4073 
  • 34a Bellina F. Rossi R. Chem. Rev.  2010,  110:  1082 
    Search in Google Scholar
  • 34b Johansson CCC. Colacot TJ. Angew. Chem. Int. Ed.  2010,  49:  676 
    Search in Google Scholar
  • 34c Culkin DA. Hartwig JF. Acc. Chem. Res.  2003,  36:  234 
    Search in Google Scholar
  • 35a Biscoe MR. Buchwald SL. Org. Lett.  2009,  11:  1773 
    Search in Google Scholar
  • 35b Hama T. Hartwig JF. Org. Lett.  2008,  10:  1545 
    Search in Google Scholar
  • 35c Jørgensen M. Lee S. Liu X. Wolkowski JP. Hartwig JF. J. Am. Chem. Soc.  2002,  124:  12557 
    Search in Google Scholar
  • 35d Moradi WA. Buchwald SL. J. Am. Chem. Soc.  2001,  123:  7996 
    Search in Google Scholar
  • 35e Lee S. Beare NA. Hartwig JF. J. Am. Chem. Soc.  2001,  123:  8410 
    Search in Google Scholar
  • 36a Culkin DA. Hartwig JF. J. Am. Chem. Soc.  2001,  123:  5816 
    Search in Google Scholar
  • 36b Culkin DA. Hartwig JF. Organometallics  2004,  23:  3398 
    Search in Google Scholar
  • 37a Chobanian HR. Liu P. Chioda MD. Guo Y. Lin LS. Tetrahedron Lett.  2007,  48:  1213 
    Search in Google Scholar
  • 37b Liu P. Lanza TJ. Jewell JP. Jones CP. Hagmann WK. Lin LS. Tetrahedron Lett.  2003,  44:  8869 
    Search in Google Scholar
  • 37c Su WP. Raders S. Verkade JG. Liao XB. Hartwig JF. Angew. Chem. Int. Ed.  2006,  45:  5852 
    Search in Google Scholar
  • 37d Kosugi M. Suzuki M. Hagiwara I. Goto K. Saitoh K. Migita T. Chem. Lett.  1982,  939 
  • 38 Hesp KD. Lundgren RJ. Stradiotto M. J. Am. Chem. Soc.  2011,  133:  5194 
    CrossrefSearch in Google Scholar
  • 39a Hartwig JF. Organotransition Metal Chemistry: From Bonding to Catalysis   University Science Books; Sausalito: 2010. 
  • 39b Müller TE. Beller M. Chem. Rev.  1998,  98:  675 
    Search in Google Scholar
  • 39c Müller TE. Hultzsch KC. Yus M. Foubelo F. Tada M. Chem. Rev.  2008,  108:  3795 
    Search in Google Scholar
  • 40a Mukherjee S. Yang JW. Hoffmann S. List B. Chem. Rev.  2007,  107:  5471 
    Search in Google Scholar
  • 40b Kuckländer U. The Chemistry of Enamines   Wiley-VCH; New York: 1994. 
  • 41a Zhang Z. Leitch DC. Lu M. Patrick BO. Schafer LL. Chem. Eur. J.  2007,  13:  2012 
    Search in Google Scholar
  • 41b Heutling A. Pohlki F. Doye S. Chem. Eur. J.  2004,  10:  3059 
    Search in Google Scholar
  • 41c Ackermann L. Organometallics  2003,  22:  4367 
    Search in Google Scholar
  • 41d Tillack A. Castro IG. Hartung CG. Beller M. Angew. Chem. Int. Ed.  2002,  41:  2541 
    Search in Google Scholar
  • 41e Walsh PJ. Baranger AM. Bergman RG. J. Am. Chem. Soc.  1992,  114:  1708 
    Search in Google Scholar
  • 42 Leitch DC. Payne PR. Dunbar CR. Schafer LL. J. Am. Chem. Soc.  2009,  131:  18246 
    CrossrefPubMedSearch in Google Scholar
  • 43 Hesp KD. Stradiotto M. J. Am. Chem. Soc.  2010,  132:  18026 
    CrossrefSearch in Google Scholar
  • 44a Lavallo V. Frey GD. Kousar S. Donnadieu B. Bertrand G. Proc. Natl. Acad. Sci. U.S.A.  2007,  104:  13569 
    Search in Google Scholar
  • 44b Lavallo V. Frey GD. Donnadieu B. Soleilhavoup M. Bertrand G. Angew. Chem. Int. Ed.  2008,  47:  5224 
    Search in Google Scholar
  • 44c Zeng XM. Frey GD. Kinjo R. Donnadieu B. Bertrand G. J. Am. Chem. Soc.  2009,  131:  8690 
    Search in Google Scholar
  • 44d Zeng XM. Frey GD. Kousar S. Bertrand G. Chem. Eur. J.  2009,  15:  3056 
    Search in Google Scholar
  • 45 Fukumoto Y. Asai H. Shimizu M. Chatani N. J. Am. Chem. Soc.  2007,  129:  13792 
    CrossrefPubMedSearch in Google Scholar
  • 46 Nishina N. Yamamoto Y. Tetrahedron  2009,  65:  1799 
    CrossrefSearch in Google Scholar
  • 47a Nishina N. Yamamoto Y. Angew. Chem. Int. Ed.  2006,  45:  3314 
    Search in Google Scholar
  • 47b Mizushima E. Hayashi T. Tanaka M. Org. Lett.  2003,  5:  3349 
    Search in Google Scholar
  • 48a Hashmi ASK. Schuster AM. Rominger F. Angew. Chem. Int. Ed.  2009,  48:  8247 
    Search in Google Scholar
  • 48b Hashmi ASK. Ramamurthi TD. Rominger F. Adv. Synth. Catal.  2010,  352:  971 
    Search in Google Scholar
  • 48c Weber D. Tarselli MA. Gagné MR. Angew. Chem. Int. Ed.  2009,  48:  5733 
    Search in Google Scholar
  • 49 Hashmi ASK. Angew. Chem. Int. Ed.  2010,  49:  5232 
    CrossrefSearch in Google Scholar
50

DalPhos ligands including Mor-DalPhos are now commercially available.