Nickel-Catalyzed Cross-Coupling of Functionalized Organo­manganese Reagents with Aryl and Heteroaryl Halides Promoted by 4-Fluorostyrene

Abstract

A catalytic system consisting of Ni(acac)₂ (5 mol%) and 4-fluorostyrene (20 mol%) allows a convenient cross-coupling of functionalized organomanganese reagents with a variety of aryl and heteroaryl halides leading to polyfunctionalized diaryl- and arylheteroarylmethane derivatives.

Key words

nickel catalysis - 4-fluorostyrene - cross-coupling - organomanganese reagents - transmetalation

• References


For selected examples see:
• 1a Normant JF. Cahiez G. In Modern Synthetic Methods . Vol. 3. Scheffold R. Wiley; Chichester: 1983: 173
• 1b Cahiez G. Actual. Chim. 1984; 7: 24
• 1c Cahiez G. An. Quim. 1995; 91: 561
• 1d Cahiez G. In Encyclopedia of Reagents for Organic Synthesis . Vol. 2. Paquette L. Wiley; Chichester: 1995: 925
• 1e Cahiez G. In Encyclopedia of Reagents for Organic Synthesis . Vol. 5. Paquette L. Wiley; Chichester: 1995: 3227
• 1f Kim S.-H. Hanson MV. Rieke RD. Tetrahedron Lett. 1996; 37: 2197
• 1g Kim S.-H. Rieke RD. Synth. Commun. 1998; 28: 1065
• 1h Kim S.-H. Rieke RD. Tetrahedron Lett. 1999; 40: 4931
• 1i Fugami K. Hibino J.-I. Nakatsukasa S. Matsubara S. Oshima K. J. Organomet. Chem. 1999; 575: 1
• 1j Kakiya H. Nishimae S. Shinokubo H. Oshima K. Tetrahedron 2001; 57: 8807
• 1k Cahiez G. Mahuteau-Betzer F. In Handbook of Functionalized Organometallics . Vol. 2. Knochel P. Wiley-VCH; Weinheim: 2005: 541
• 1l Cahiez G. Duplais C. Buendia J. Chem. Rev. 2009; 109: 1434
• 1m Kim S.-H. Rieke RD. Molecules 2010; 15: 8006
• 1n Cahiez G. Gager O. In Chemistry of Organomanganese Compounds . Rappoport Z. Marek I. Wiley; Chichester: 2011: 305
• 2a Cahiez G. Masuda A. Bernard D. Normant JF. Tetrahedron Lett. 1976; 36: 3155
• 2b Friour G. Alexakis A. Cahiez G. Normant JF. Tetrahedron 1984; 40: 683
• 2c Friour G. Cahiez G. Normant JF. Synthesis 1985; 50
• 2d Ritter K. Hanack M. Tetrahedron Lett. 1985; 26: 1285
• 2e Boche G. Eiben R. Tetrahedron Lett. 1985; 26: 1289
• 3 Quinio P. Benischke AD. Moyeux A. Cahiez G. Knochel P. Synlett 2015; 26: 514
• 4a Kauffmann T. Bisling M. Tetrahedron Lett. 1984; 25: 293
• 4b Cahiez G. Alami M. Tetrahedron Lett. 1986; 27: 569
• 4c Cahiez G. Alami M. Tetrahedron Lett. 1989; 30: 3541
• 4d Cahiez G. Alami M. J. Organomet. Chem. 1990; 397: 291
• 4e Namboothiri IN. N. Hassner A. J. Organomet. Chem. 1996; 518: 69
• 4f Yorimitsu H. Hayashi Y. Tang J. Shinokubo H. Oshima K. Bull. Chem. Soc. Jpn. 1997; 70: 2297
• 5a Peng Z. Li N. Sun X. Wang F. Xu L. Jiang C. Song L. Yan Z.-F. Org. Biomol. Chem. 2014; 12: 7800
• 5b Haas D. Hammann JM. Moyeux A. Cahiez G. Knochel P. Synlett 2015; 26: 1515
• 6a Wunderlich SH. Kienle M. Knochel P. Angew. Chem. Int. Ed. 2009; 121: 7392
• 6b Peng Z. Knochel P. Org. Lett. 2011; 13: 3198
• 7 Benischke AD. Breuillac AJ. A. Moyeux A. Cahiez G. Knochel P. Synlett 2016; 27: 471
• 8 Hofmayer MS. Hammann JM. Haas D. Knochel P. Org. Lett. 2016; 18: 6456

For recent examples, see:
• 9a Cherney AH. Reisman SE. J. Am. Chem. Soc. 2014; 136: 14365
• 9b Zhu F. Wang Z.-X. J. Org. Chem. 2014; 79: 4285
• 9c Kadunce NT. Reisman SE. J. Am. Chem. Soc. 2015; 137: 10480
• 9d Tao J.-L. Wang Z.-X. Eur. J. Org. Chem. 2015; 6534
• 9e Anka-Lufford LL. Huihui KM. M. Gower NJ. Ackermann LG. Weix DJ. Chem. Eur. J. 2016; 22: 11564
• 9f Chu CK. Liang Y. Fu GC. J. Am. Chem. Soc. 2016; 138: 6404
• 9g Tobisu M. Takahira T. Morioka T. Chatani N. J. Am. Chem. Soc. 2016; 138: 6711
• 9h Huihui KM. M. Shrestha R. Weix D. J. Org. Lett. 2017; 19: 340
• 9i Choi J. Fu GC. Science 2017; 356: 152
• 9j Mu X. Shibata Y. Makida Y. Fu GC. Angew. Chem. Int. Ed. 2017; 56: 5821

For selected reviews, see:
• 10a Phapale VB. Cardenas DJ. Chem. Soc. Rev. 2009; 38: 1598
• 10b Rosen BM. Quasdorf KW. Wilson DA. Zhang N. Resmerita A.-M. Garg NK. Percec V. Chem. Rev. 2011; 111: 1346
• 10c Jana R. Pathak TP. Sigman MS. Chem. Rev. 2011; 111: 1417
• 10d Tobisu M. Chatani N. Acc. Chem. Res. 2015; 48: 1717
• 10e Tollefson EJ. Hanna LE. Jarvo ER. Acc. Chem. Res. 2015; 48: 2344
• 11 Leleu A. Fort Y. Schneider R. Adv. Synth. Catal. 2006; 348: 1086
• 12 Liu N. Wang Z.-X. Adv. Synth. Catal. 2012; 354: 1641
• 13 Cahiez G. Laboue B. Tetrahedron Lett. 1989; 30: 7369
• 14 Krasovskiy A. Knochel P. Synthesis 2006; 890
• 15a Kuzmina OM. Steib AK. Markiewicz JT. Flubacher D. Knochel P. Angew. Chem. Int. Ed. 2013; 52: 4945
• 15b Kuzmina OM. Steib AK. Fernandez S. Boudot W. Markiewicz JT. Knochel P. Chem. Eur. J. 2015; 21: 8242
• 16 Hammann JM. Haas D. Tüllmann C.-P. Karaghiosoff K. Knochel P. Org. Lett. 2016; 18: 4778
• 17a Giovannini R. Stüdemann T. Dussin G. Knochel P. Angew. Chem. Int. Ed. 1998; 37: 2387
• 17b Giovannini R. Stüdemann T. Devasagayaraj A. Dussin G. Knochel P. J. Org. Chem. 1999; 64: 3544
• 17c Piber M. Jensen AE. Rottländer M. Knochel P. Org. Lett. 1999; 1: 1323
• 17d Jensen AE. Knochel P. J. Org. Chem. 2002; 67: 79
• 17e Korn TJ. Knochel P. Angew. Chem. Int. Ed. 2005; 44: 2947

For recent examples, see:
• 18a Guisan-Ceinos M. Soler-Yanes R. Collado-Sanz D. Phapale VB. Bunuel E. Cardenas DJ. Chem. Eur. J. 2013; 19: 8405
• 18b Denmark SE. Cresswell AJ. J. Org. Chem. 2013; 78: 12593
• 18c Hammann JM. Steib AK. Knochel P. Org. Lett. 2014; 16: 6500
• 18d Hammann JM. Haas D. Knochel P. Angew. Chem. Int. Ed. 2015; 54: 4478
• 18e Magano J. Monfette S. ACS Catal. 2015; 5: 3120
• 19a Cahiez G. Alami M. Tetrahedron 1989; 45: 4163
• 19b Cahiez G. Razafintsalama L. Laboue B. Chau F. Tetrahedron Lett. 1998; 39: 849