Synthesis, Inhaltsverzeichnis Synthesis 2019; 51(02): 538-544DOI: 10.1055/s-0037-1610251 paper © Georg Thieme Verlag Stuttgart · New York Copper-Catalyzed NaBAr4-Based N-Arylation of Amines Qin Yang , Xiaoli Lei , Zhijian Yin , Zhihong Deng , Yiyuan Peng * Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Using NaBAr4 as an arylating agent, the formation of carbon–heteroatom bonds by a Cham–Lam cross-coupling reaction in the presence of catalytic copper(II) acetate monohydrate in acetonitrile at room temperature under air is described. The investigation of reaction scope suggests that several aliphatic and aromatic amines are compatible. In particular, the reaction of alkylamine and NaBAr4 proceeds smoothly to offer the corresponding products in good to excellent yields. Keywords KeywordsCham–Lam cross-coupling reaction - amine - copper acetate monohydrate - tetraphenylborate - N-phenylation Volltext Referenzen References 1a Lindley J. Tetrahedron 1984; 40: 1433 1b Kiyomori A. Marcoux J.-F. Buchwald SL. Tetrahedron Lett. 1999; 40: 2657 2a Chan DM. T. Monaco KL. Wang RP. Winters MP. Tetrahedron Lett. 1998; 39: 2933 2b Evans DA. Katz JL. West TR. Tetrahedron Lett. 1998; 39: 2937 2c Lam PY. S. Clark CG. Saubern S. Adams J. Winters MP. Chan DM. T. Combs A. Tetrahedron Lett. 1998; 39: 2941 2d Lam PY. S. Clark CG. Saubern S. Adams J. Averill KM. Chan DM. T. Combs A. Synlett 2000; 674 3a Ma XP. Liu FP. Mo DL. Chin. J. Org. Chem. 2017; 37: 1069 3b Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400 For some recent reviews, see: 4a Qiao JX. Lam PY. S. Synthesis 2011; 829 4b Rao KS. Wu TS. Tetrahedron 2012; 68: 7735 5 Elliott GI. Konopelski JP. Org. Lett. 2000; 20: 3055 6 Sorenson RJ. J. Org. Chem. 2000; 65: 7747 7 Lam PY. S. Deudon S. Averill KM. Li RH. He MY. DeShong P. Clark CG. J. Am. Chem. Soc. 2000; 122: 7600 8 Kang SK. Lee SH. Lee D. Synlett 2000; 1022 9a Collman JP. Zhong M. Org. Lett. 2000; 9: 1233 9b Collman JP. Zhong M. Zeng L. Costanzo S. J. Org. Chem. 2001; 66: 1528 10 Lam YS. P. Vincent G. Clark CG. Deudon S. Jadhav PK. Tetrahedron Lett. 2001; 42: 3415 11 Antilla JC. Buchwald SL. Org. Lett. 2001; 3: 2077 12a Quach TD. Batey RA. Org. Lett. 2003; 5: 1381 12b Quach TD. Batey RA. Org. Lett. 2003; 5: 4397 13 Chiang GH. Olsson T. Org. Lett. 2004; 6: 3079 14a Vantourout JC. Miras HN. Isidro-Liobe A. Sproules S. Watson AJ. B. J. Am. Chem. Soc. 2017; 139: 4769 14b Vantourout JC. Law RP. Isidro-Liobe A. Atkinson SJ. Watson AJ. B. J. Org. Chem. 2016; 81: 3942 15a Legzdins P. Richter-Addo GB. Einstein FW. B. Jones R. Organometallics 1990; 9: 431 15b Bonnesen PV. Puckett CL. Honeychuck RV. Hersh WH. J. Am. Chem. Soc. 1989; 111: 6070 16a Legros JY. Fiaud JC. Tetrahedron Lett. 1990; 31: 7453 16b Hamasaka G. Sakuraiab F. Uozumi Y. Chem. Commun. 2015; 51: 3886 17 Kurosawa H. Ogoshi S. Kawasaki Y. Murai S. Ikeda I. J. Am. Chem. Soc. 1990; 112: 2813 18a Catellani M. Chiusoli GP. Concari S. Tetrahedron 1989; 45: 5263 18b Ciattini PG. Morera E. Ortar G. Tetrahedron Lett. 1992; 33: 4815 18c Bumagin NA. Bykoy VV. Tetrahedron 1997; 53: 14437 18d Villemin D. Gömez-Escalonilla MJ. Saint-Clair JF. Tetrahedron Lett. 2001; 42: 635 18e Leadbeater NE. Marco M. J. Org. Chem. 2003; 68: 5660 18f Wang JX. Yang YH. Wei BG. Synth. Commun. 2004; 34: 2063 18g Lu G. Franzén R. Zhang Q. Xu Y. Tetrahedron Lett. 2005; 46: 4255 18h Liu G. Cai MZ. Catal. Commun. 2007; 8: 251 18i Zhao H. Zheng GM. Sheng SR. Cai MZ. Catal. Commun. 2009; 11: 158 18j Vasu D. Hausmann JN. Saito H. Yanagi T. Yorimitsu H. Osuka A. Asian J. Org. Chem. 2017; 6: 1390 19 Zeng H. Hua R. J. Org. Chem. 2008; 73: 558 20a Shintani R. Tsutsumi Y. Nagaosa M. Nishimura T. Hayashi T. J. Am. Chem. Soc. 2009; 131: 13588 20b Shintani R. Isobe S. Takeda M. Hayashi T. Angew. Chem. Int. Ed. 2010; 49: 3795 21a Vasu D. Yorimitsu H. Osuka A. Angew. Chem. Int. Ed. 2015; 54: 7162 21b Vasu D. Yorimitsu H. Osuka A. Synthesis 2015; 47: 3286 21c Shintani R. Takeda M. Tsuji T. Hayashi T. J. Am. Chem. Soc. 2010; 132: 13168 22a Wolfe JP. Buchwald SL. J. Org. Chem. 1997; 62: 6066 22b Kantam ML. Venkanna GT. Sridhar C. Sreedhar B. Choudary BM. J. Org. Chem. 2006; 71: 9522 22c Kosynkin DV. Tour JM. Org. Lett. 2001; 3: 991 22d Kataoka N. Shelby Q. Stambuli JP. Hartwig JF. J. Org. Chem. 2002; 67: 5553 22e Gao CY. Yang ML. J. Org. Chem. 2008; 73: 1624 22f Litvinov VS. Voprosy Khim. Khim. Tekhnol. 1978; 52: 34 22g Swapna KA. Kumar V. Reddy VP. Rao KV. J. Org. Chem. 2009; 74: 7514 22h Daniels DG. H. Naylor FT. Saunders BC. J. Chem. Soc. 1951; 3433 22i Naber JR. Buchwald SL. Angew. Chem. Int. Ed. 2010; 49: 9469 22j Abe K. Takahashi M. Kunugi A. Chem. Exp. 1990; 5: 385 22k Hajra A. Wei Y. Yoshikai N. Org. Lett. 2012; 14: 5488 22l Chen C. Yang LM. J. Org. Chem. 2007; 72: 6324 Zusatzmaterial Zusatzmaterial Supporting Information
