Anti-Markovnikov Hydrogermylation of Alkenes via Lewis Acid Catalysis

被引：11

作者：

Selmani, Aymane ^{[1
]}

Schoenebeck, Franziska ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

来源：

SYNTHESIS-STUTTGART | 2023年 / 55卷 / 11期

基金：

欧洲研究理事会;

关键词：

organogermanes; hydrogermylation; Lewis acid; catalysis; anti-Markovnikov; C-H FUNCTIONALIZATION; BIARYL SYNTHESIS; ACCESS;

D O I：

10.1055/a-2036-3868

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct hydrogermylation of alkenes under Lewis acid catalysis is reported. The use of borane B(C6F5)3 as a catalyst allows for a mild, metal-free hydrogermylation of alkenes and concomitant reduction of ketones and aldehydes. Regardless of electronic biases, anti-Markovnikov hydrogermylation is observed in high yields. Moreover, the process is scalable and proceeds under mild conditions at room temperature.

引用

页码：1792 / 1798

页数：7

共 34 条

[1] Lewis Acid-Promoted Addition of 1,3-Bis(silyl)propenes to Aldehydes: A Route to 1,3-Dienes
Borg, Tessie
Tuzina, Pavel
Somfai, Peter
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) : 8070 - 8075
[2] Metal-catalyzed rearrangement of homoallylic ethers to silylmethyl allylic silanes in the presence of a di-tert-butylsilylene source
Cleary, PA
Woerpel, KA
[J]. ORGANIC LETTERS, 2005, 7 (24) : 5531 - 5533
[3] Orthogonal and Modular Arylation of Alkynylgermanes
Dahiya, Amit
Schoenebeck, Franziska
[J]. ACS CATALYSIS, 2022, 12 (13) : 8048 - 8054
[4] Gold-Catalyzed Chemoselective Couplings of Polyfluoroarenes with Aryl Germanes and Downstream Diversification
Dahiya, Amit
Fricke, Christoph
Schoenebeck, Franziska
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (17) : 7754 - 7759
[5] Palladium-catalyzed cross-coupling reaction by means of organogermanium trichlorides
Enokido, T
Fugami, K
Endo, M
Kameyama, M
Kosugi, M
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1685 - 1688
[6] Organogermanes as Orthogonal Coupling Partners in Synthesis and Catalysis
Fricke, Christoph
Schoenebeck, Franziska
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (11) : 2715 - 2725
[7] Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations
Fricke, Christoph
Deckers, Kristina
Schoenebeck, Franziska
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (42) : 18717 - 18722
[8] Gold-Catalyzed C-H Functionalization with Aryl Germanes
Fricke, Christoph
Dahiya, Amit
Reid, William B.
Schoenebeck, Franziska
[J]. ACS CATALYSIS, 2019, 9 (10): : 9231 - +
[9] 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
[10] Nickel-Catalyzed Reductive Csp3-Ge Coupling of Alkyl Bromides with Chlorogermanes
Guo, Peng
Pang, Xiaobo
Wang, Ke
Su, Pei-Feng
Pan, Qiu-Quan
Han, Guan-Yu
Shen, Qian
Zhao, Zhen-Zhen
Zhang, Wenhua
Shu, Xing-Zhong
[J]. ORGANIC LETTERS, 2022, 24 (09) : 1802 - 1806

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