Nickel-Catalyzed Reductive Csp3-Ge Coupling of Alkyl Bromides with Chlorogermanes

被引：35

作者：

Guo, Peng ^{[1
,2
]}

Pang, Xiaobo ^{[1
]}

Wang, Ke ^{[1
]}

Su, Pei-Feng ^{[1
]}

Pan, Qiu-Quan ^{[1
]}

Han, Guan-Yu ^{[1
]}

Shen, Qian ^{[1
]}

Zhao, Zhen-Zhen ^{[1
]}

Zhang, Wenhua ^{[2
]}

Shu, Xing-Zhong ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem SKLAOC, Lanzhou 730000, Peoples R China

[2] Lanzhou Univ, Sch Life Sci, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 09期

基金：

中国国家自然科学基金;

关键词：

ARYL HALIDES; OXIDATIVE ADDITION; ACCESS; FUNCTIONALIZATION; SILYLATION; GERMANIUM; BONDS;

D O I：

10.1021/acs.orglett.2c00207

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reductive cross-coupling provides facile access to organogermanes, but it remains largely unexplored. Herein we report a nickel-catalyzed reductive Csp(3)-Ge coupling of alkyl bromides with chlorogermanes. This work has established a new method for producing alkylgermanes. The reaction proceeds under very mild conditions and tolerates various functionalities including ether, alcohol, alkene, nitrile, amine, ester, phosphonates, amides, ketone, and aldehyde. The application of this method to the modification of bioactive molecules is demonstrated.

引用

页码：1802 / 1806

页数：5

共 52 条

[11] Gold-Catalyzed C-H Functionalization with Aryl Germanes
Fricke, Christoph
Dahiya, Amit
Reid, William B.
Schoenebeck, Franziska
[J]. ACS CATALYSIS, 2019, 9 (10): : 9231 - +
[12] Orthogonal Nanoparticle Catalysis with Organogermanes
Fricke, Christoph
Sherborne, Grant J.
Funes-Ardoiz, Ignacio
Senol, Erdem
Guven, Sinem
Schoenebeck, Franziska
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (49) : 17788 - 17795
[13] Increased Hydrophobicity and Estrogenic Activity of Simple Phenols with Silicon and Germanium-Containing Substituents
Fujii, Shinya
Miyajima, Yu
Masuno, Hiroyuki
Kagechika, Hiroyuki
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (01) : 160 - 166
[14] Goldfogel MJ, 2020, NICKEL CATALYSIS IN ORGANIC SYNTHESIS: METHODS AND REACTIONS, P183
[15] Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis
Guo, Peng
Wang, Ke
Jin, Wen-Jie
Xie, Hao
Qi, Liangliang
Liu, Xue-Yuan
Shu, Xing-Zhong
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (01) : 513 - 523
[16] Reductive Coupling between C-N and C-O Electrophiles
He, Rong-De
Li, Chun-Ling
Pan, Qiu-Quan
Guo, Peng
Liu, Xue-Yuan
Shu, Xing-Zhong
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (32) : 12481 - 12486
[17] Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols
Jia, Xue-Gong
Guo, Peng
Duan, Jicheng
Shu, Xing-Zhong
[J]. CHEMICAL SCIENCE, 2018, 9 (03) : 640 - 645
[18] Periodic Trends in Organic Functionalization of Group IV Semiconductor Surfaces
Kachian, Jessica S.
Wong, Keith T.
Bent, Stacey F.
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (02) : 346 - 355
[19] Experimental and theoretical studies of Si-Cl and Ge-Cl σ-bond activation reactions by iridium-hydride
Kameo, H.
Ikeda, K.
Sakaki, S.
Takemoto, S.
Nakazawa, H.
Matsuzaka, H.
[J]. DALTON TRANSACTIONS, 2016, 45 (18) : 7570 - 7580
[20] Pd/Ni-Catalyzed Germa-Suzuki coupling via dual Ge-F bond activation
Kameo, Hajime
Mushiake, Akihiro
Isasa, Tomohito
Matsuzaka, Hiroyuki
Bourissou, Didier
[J]. CHEMICAL COMMUNICATIONS, 2021, 57 (41) : 5004 - 5007

← 1 2 3 4 5 6 →