Cobalt-Catalyzed Negishi Cross-Coupling Reactions of (Hetero)Arylzinc Reagents with Primary and Secondary Alkyl Bromides and Iodides

被引：78

作者：

Hammann, Jeffrey M. ^{[1
]}

Haas, Diana ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 15期

关键词：

cobalt; cross-coupling; heterocycles; metalation; zinc; DIRECTED ORTHO-METALATION; ARYL GRIGNARD-REAGENTS; CENTER-DOT-LICL; 6-HALO-1-HEXENE DERIVATIVES; CHEMOSELECTIVE METALATION; HALIDES; ZINCATION; AMIDE; BASE; FUNCTIONALIZATION;

D O I：

10.1002/anie.201411960

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a cobalt-catalyzed cross-coupling of di(hetero)arylzinc reagents with primary and secondary alkyl iodides or bromides using THF-soluble CoCl(2)2LiCl and TMEDA as a ligand, which leads to the corresponding alkylated products in up to 88% yield. A range of functional groups (e.g. COOR, CN, CF3, F) are tolerated in these substitution reactions. Remarkably, we do not observe rearrangement of secondary alkyl iodides to unbranched products. Additionally, the use of cyclic TBS-protected iodohydrins leads to trans-2-arylcyclohexanol derivatives in excellent diastereoselectivities (up to d.r.=99:1).

引用

页码：4478 / 4481

页数：4

共 50 条

[31] Cross-Coupling of Aryltrimethylammonium Iodides with Arylzinc Reagents Catalyzed by Amido Pincer Nickel Complexes
Zhang, Xue-Qi
Wang, Zhong-Xia
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07): : 3658 - 3663
[32] Iron-Catalyzed Cross-Coupling Reactions between Arylzinc Reagents and Alkyl Halides Bearing β-Fluorines
Lin, Xiaowei
Zheng, Feng
Qing, Feng-Ling
ORGANOMETALLICS, 2012, 31 (04) : 1578 - 1582
[33] Stabilized Arylzinc Iodides in Negishi Acylative Cross-Coupling: A Modular Synthesis of Chalcones
Pierige, Michele
Iuliano, Anna
Angelici, Gaetano
Casotti, Gianluca
ORGANICS, 2022, 3 (02): : 87 - 94
[34] Cobalt-Catalyzed Cross-Coupling of α-Bromo Amides with Grignard Reagents
Barde, E.
Guerinot, A.
Cossy, J.
ORGANIC LETTERS, 2017, 19 (22) : 6068 - 6071
[35] Cobalt-catalyzed cross-coupling reaction of chloropyridines with Grignard reagents
Ohmiya, H
Yorimitsu, H
Oshima, K
CHEMISTRY LETTERS, 2004, 33 (10) : 1240 - 1241
[36] Cobalt-Catalyzed Cross-Coupling Reactions Aryl Halides
Gosmini, Corinne
Moncomble, Aurelien
ISRAEL JOURNAL OF CHEMISTRY, 2010, 50 (5-6) : 568 - 576
[37] Cobalt-Catalyzed Enantioselective Negishi Cross-Coupling of Racemic α-Bromo Esters with Arylzincs
Liu, Feipeng
Zhong, Jiangchun
Zhou, Yun
Gao, Zidong
Walsh, Patrick J.
Wang, Xueyang
Ma, Sijie
Hou, Shicong
Liu, Shangzhong
Wang, Minan
Wang, Min
Bian, Qinghua
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (09) : 2059 - +
[38] Cobalt-catalyzed cross-coupling of alkynyl Grignard reagents with alkenyl triflates
Shirakawa, Eiji
Sato, Takahiro
Imazaki, Yusuke
Kimura, Takahiro
Hayashi, Tamio
CHEMICAL COMMUNICATIONS, 2007, (43) : 4513 - 4515
[39] Cobalt-catalyzed cross-coupling reactions of heterocyclic chlorides with arylmagnesium halides and of polyfunctionalized arylcopper reagents with aryl bromides, chlorides, fluorides and tosylates
Korn, Tobias J.
Schade, Matthias A.
Cheemala, Murthy N.
Wirth, Stefan
Guevara, Simon A.
Cahiez, Gerard
Knochel, Paul
SYNTHESIS-STUTTGART, 2006, (21): : 3547 - 3574
[40] Cross-Couplings of Unactivated Secondary Alkyl Halides: Room-Temperature Nickel-Catalyzed Negishi Reactions of Alkyl Bromides and Iodides
1600, American Chemical Society (125):

← 1 2 3 4 5 →