Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents

被引：101

作者：

Chierchia, Matteo ^{[1
]}

Xu, Peilin ^{[1
]}

Lovinger, Gabriel J. ^{[1
]}

Morken, James P. ^{[1
]}

机构：

[1] Boston Coll, Dept Chem, 2609 Beacon St, Chestnut Hill, MA 02467 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 40期

关键词：

boron; catalysis; cross-coupling; nickel; radical reactions; CATALYZED INTERMOLECULAR TRIFLUOROMETHYLARYLATION; POLAR CROSSOVER REACTIONS; REDUCTIVE DICARBOFUNCTIONALIZATION; UNACTIVATED OLEFINS; HALIDES; CYCLIZATION; STYRENES; ESTERS; 1,2-DIFUNCTIONALIZATION; DIFUNCTIONALIZATION;

D O I：

10.1002/anie.201908029

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A hybrid transition-metal/radical process is described that results in the addition of organozinc reagents and alkyl halides across alkenyl boron reagents in an enantioselective catalytic fashion. The reaction can be accomplished both intermolecularly and intramolecularly, providing useful product yields and high enantioselectivities in both manifolds.

引用

页码：14245 / 14249

页数：5

共 50 条

[41] Pd-catalyzed Fukuyama cross-coupling of secondary organozinc reagents for the direct synthesis of unsymmetrical ketones
Cherney, Alan H.
Reisman, Sarah E.
TETRAHEDRON, 2014, 70 (20) : 3259 - 3265
[42] Scaled-Up Transition-Metal-Catalyzed Cross-Coupling Reactions of Thioether-Substituted N-Heterocycles with Organozinc Reagents
Metzger, Albrecht
Melzig, Laurin
Knochel, Paul
SYNTHESIS-STUTTGART, 2010, (16): : 2853 - 2858
[43] Iron-Catalyzed Cross-Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow
Deng, Yuchao
Wei, Xiao-Jing
Wang, Xiao
Sun, Yuhan
Noel, Timothy
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (64) : 14532 - 14535
[44] Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides
Cahiez, Gerard
Gager, Olivier
Buendia, Julien
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (07) : 1278 - 1281
[45] Iron-catalyzed cross-coupling of heteroaromatic tosylates with alkyl and aryl Grignard reagents
Chen, Xu
Quan, Zheng-Jun
Wang, Xi-Cun
APPLIED ORGANOMETALLIC CHEMISTRY, 2015, 29 (05) : 296 - 300
[46] Nickel-Catalyzed Cross-Coupling of Bromodifluoromethylphosphonates with Arylboron Reagents
Kuriyama, Masami
Maeda, Genki
Kamata, Kazuya
Kodama, Yusuke
Yamamoto, Kosuke
Onomura, Osamu
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (01) : 116 - 121
[47] Carbon-Carbon π Bonds as Conjunctive Reagents in Cross-Coupling
Derosa, Joseph
Tran, Van T.
van der Puyl, Vincent A.
Engle, Keary M.
ALDRICHIMICA ACTA, 2018, 51 (01) : 21 - 32
[48] Iron-Catalyzed Cross-Coupling of Thioesters and Organomanganese Reagents
Geiger, Valentin Jacob
Lefevre, Guillaume
Fleischer, Ivana
CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (62)
[49] Single electron transfer-induced coupling of alkynylzinc reagents with aryl and alkenyl iodides
Okura, Keisho
Kawashima, Hitomi
Tamakuni, Fumiko
Nishida, Naoya
Shirakawa, Eiji
CHEMICAL COMMUNICATIONS, 2016, 52 (97) : 14019 - 14022
[50] Direct -Selective Cross-Coupling of Alkenyl Gold Complexes with Alkyl Electrophiles
Nguyen, Julia
Duncan, Nicole
Lalic, Gojko
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (35) : 5803 - 5806

← 1 2 3 4 5 →