β-aminoethyltrifluoroborates:: Efficient aminoethylations via Suzuki-Miyaura cross-coupling

被引:50
作者
Molander, Gary A. [1 ]
Vargas, Fabricio [1 ]
机构
[1] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ol062610v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A set of phenethylamines has been successfully prepared via Suzuki-Miyaura cross-coupling of diverse potassium beta-aminoethyltrifluoroborates with aryl halides. The potassium beta-aminoethyltrifluoroborates were easily prepared via hydroboration of enamine and enamide precursors.
引用
收藏
页码:203 / 206
页数:4
相关论文
共 21 条
[1]   DIRECT COUPLING OF FUNCTIONALIZED ORGANOLITHIUM COMPOUNDS WITH ARYL AND VINYL HALIDES [J].
BARLUENGA, J ;
MONTSERRAT, JM ;
FLOREZ, J .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5976-5980
[2]   β-phenylethylamines and the isoquinoline alkaloids [J].
Bentley, KW .
NATURAL PRODUCT REPORTS, 1999, 16 (03) :367-388
[3]   PHENETHYLAMINES VIA HECK ARYLATION OF A NEW VINYLAMINE EQUIVALENT [J].
BUSACCA, CA ;
JOHNSON, RE ;
SWESTOCK, J .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) :3299-3303
[4]   Potassium trifluoro(organo)borates: New perspectives in organic chemistry [J].
Darses, S ;
Genet, JP .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) :4313-4327
[5]   Sequential catalytic asymmetric Heck-iminium ion cyclization:: Enantioselective total synthesis of the Strychnos alkaloid minfiensine [J].
Dounay, AB ;
Overman, LE ;
Wrobleski, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) :10186-10187
[6]   PREPARATION AND REACTIVITY OF CHIRAL BETA-AMIDO-ALKYLZINC IODIDES AND RELATED CONFIGURATIONALLY STABLE ZINC ORGANOMETALLICS [J].
DUDDU, R ;
ECKHARDT, M ;
FURLONG, M ;
KNOESS, HP ;
BERGER, S ;
KNOCHEL, P .
TETRAHEDRON, 1994, 50 (08) :2415-2432
[7]   Indol-2-one intermediates:: Mechanistic evidence and synthetic utility.: Total syntheses of (±)-flustramines A and C [J].
Fuchs, JR ;
Funk, RL .
ORGANIC LETTERS, 2005, 7 (04) :677-680
[8]   Efficient synthesis of protected β-phenylethylamines, enantiomerically pure protected β-phenyl-α-benzylethylamines and β-phenyl-α-isopropylethylamines using organozinc chemistry [J].
Hunter, C ;
Jackson, RFW ;
Rami, HK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (02) :219-223
[9]   Di(isopropylprenyl)borane: A new hydroboration reagent for the synthesis of alkyl and alkenyl boronic acids [J].
Kalinin, AV ;
Scherer, S ;
Snieckus, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (29) :3399-3404
[10]   A Suzuki coupling method for directly introducing a protected β-aminoethyl group into arenes and alkenes.: Convenient synthesis of phenethyl and homoallylic amines [J].
Kamatani, A ;
Overman, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23) :8743-8744