One-Pot Primary Aminomethylation of Aryl and Heteroaryl Halides with Sodium Phthalimidomethyltrifluoroborate

被引:23
作者
Murai, Norio [1 ,2 ]
Miyano, Masayuki [2 ]
Yonaga, Masahiro [1 ,2 ]
Tanaka, Keigo [2 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
[2] Eisai & Co Ltd, Discovery Res Labs, Tsukuba, Ibaraki 3002635, Japan
关键词
CHEMOSELECTIVE ACYLATION; REDUCTIVE AMINATION; AMINES; DOCKING;
D O I
10.1021/ol301037s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot primary aminomethylation of aryl halides, triflates, mesylates, and tosylates via Suzuki-Miyaura cross-coupling reactions with sodium phthalimidomethyltrifluoroborate followed by deamidation with ethylenediamine is reported.
引用
收藏
页码:2818 / 2821
页数:4
相关论文
共 38 条
[1]  
[Anonymous], 2012, Verona Pharma reports bronchodilator data with RPL554 in COPD patients at the 2012 European Respiratory Society, Patent No. 20090197871
[2]   Efficient catalyst for the Suzuki-Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides [J].
Barder, TE ;
Buchwald, SL .
ORGANIC LETTERS, 2004, 6 (16) :2649-2652
[3]  
Benington F., 1956, J ORG CHEM, V55, P1545
[4]   A novel efficient and chemoselective method for the reduction of nitriles using the system silane/oxo-rhenium complexes [J].
Cabrita, Ivania ;
Fernandes, Ana C. .
TETRAHEDRON, 2011, 67 (42) :8183-8186
[5]   Silicon switch approach in TRPV1 antagonist MK-056 and its analogues [J].
Chang, Minsun ;
Park, Seol-Rin ;
Kim, Juhyun ;
Jang, Mijung ;
Park, Jeong Hyun ;
Park, Ji Eun ;
Park, Hyeung-Geun ;
Suh, Young-Ger ;
Jeong, Yeon Su ;
Park, Young-Ho ;
Kim, Hee-Doo .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (01) :111-116
[6]   Two Iron Catalysts are Better than One: A General and Convenient Reduction of Aromatic and Aliphatic Primary Amides [J].
Das, Shoubhik ;
Wendt, Bianca ;
Moeller, Konstanze ;
Junge, Kathrin ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (07) :1662-1666
[7]   Synthesis and cross-coupling reactions of imidomethyltrifluoroborates with aryl chlorides [J].
Devulapally, Rammohan ;
Fleury-Bregeot, Nicolas ;
Molander, Gary A. ;
Seapy, Dave G. .
TETRAHEDRON LETTERS, 2012, 53 (09) :1051-1055
[8]  
Greene T.W., 2007, PROTECTIVE GROUPS OR
[9]   Synthesis of primary amines: First homogeneously catalyzed reductive amination with ammonia [J].
Gross, T ;
Seayad, AM ;
Ahmad, M ;
Beller, M .
ORGANIC LETTERS, 2002, 4 (12) :2055-2058
[10]  
Heinen AW, 2000, EUR J ORG CHEM, V2000, P2501