α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis

被引：122

作者：

El Khatib, Mirna ^{[1
]}

Massarico Serafim, Ricardo Augusto ^{[1
,2
]}

Molander, Gary A. ^{[1
]}

机构：

[1] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA

[2] Univ Sao Paulo, FCF USP, Fac Pharmaceut Sci, Dept Pharm, BR-05508 Sao Paulo, Brazil

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 01期

关键词：

amino acids; cross-coupling; heterocycles; nickel; photochemistry; BOC-PROTECTED AMINOMETHYLTRIFLUOROBORATE; SINGLE-ELECTRON TRANSMETALATION; LIGHT-MEDIATED ADDITION; AMINO-ACIDS; CARBOXYLIC-ACIDS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITIONS; RADICALS; SECONDARY; ARYL;

D O I：

10.1002/anie.201506147

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct access to complex, enantiopure benzylamine architectures using a synergistic iridium photoredox/nickel cross-coupling dual catalysis strategy has been developed. New C(sp(3)) C(sp(2)) bonds are forged starting from abundant and inexpensive natural amino acids.

引用

页码：254 / 258

页数：5

共 44 条

[1]

Baxter E.W., 2002, ORGANIC REACTIONS, V59, P1, DOI [DOI 10.1002/0471264180.0R059.01, DOI 10.1002/0471264180.OR059.01]

[2] Boronic Acids and Esters in the Petasis-Borono Mannich Multicomponent Reaction [J].

Candeias, Nuno R. ;

Montalbano, Francesco ;

Cal, Pedro M. S. D. ;

Gois, Pedro M. P. .

CHEMICAL REVIEWS, 2010, 110 (10) :6169-6193

[3] Photocatalytic Decarboxylative Reduction of Carboxylic Acids and Its Application in Asymmetric Synthesis [J].

Cassani, Carlo ;

Bergonzini, Giulia ;

Wallentin, Carl-Johan .

ORGANIC LETTERS, 2014, 16 (16) :4228-4231

[4]

CHENG PTW, 2001, Patent No. 0121602

[5] Redox-economical radical generation from organoborates and carboxylic acids by organic photoredox catalysis [J].

Chinzei, Tatsuya ;

Miyazawa, Kazuki ;

Yasu, Yusuke ;

Koike, Takashi ;

Akita, Munetaka .

RSC ADVANCES, 2015, 5 (27) :21297-21300

[6] Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin [J].

Chu, Lingling ;

Ohta, Chisa ;

Zuo, Zhiwei ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (31) :10886-10889

[7] Photoredox Catalysis in a Complex Pharmaceutical Setting: Toward the Preparation of JAK2 Inhibitor LY2784544 [J].

Douglas, James J. ;

Cole, Kevin P. ;

Stephenson, Corey R. J. .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23) :11631-11643

[8] Enantioselective Conjugate Additions of α-Amino Radicals via Cooperative Photoredox and Lewis Acid Catalysis [J].

Espelt, Laura Ruiz ;

McPherson, Iain S. ;

Wiensch, Eric M. ;

Yoon, Tehshik P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) :2452-2455

[9] Rapid and Efficient Access to Secondary Arylmethylamines [J].

Fleury-Bregeot, Nicolas ;

Raushel, Jessica ;

Sandrock, Deidre L. ;

Dreher, Spencer D. ;

Molander, Gary A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) :9564-9570

[10] Hydrogen Autotransfer in the N-Alkylation of Amines and Related Compounds using Alcohols and Amines as Electrophiles [J].

Guillena, Gabriela ;

Ramon, Diego J. ;

Yus, Miguel .

CHEMICAL REVIEWS, 2010, 110 (03) :1611-1641

← 1 2 3 4 5 →