Nickel‐Catalyzed Reductive C−Ge Coupling of Aryl/Alkenyl Electrophiles with Chlorogermanes. Issue 51 (9th November 2021)

• Record Type: Journal Article
• Authors: Su, Pei‐Feng; Wang, Ke; Peng, Xuejing; Pang, Xiaobo; Guo, Peng; Shu, Xing‐Zhong
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 51(2021)
• Page Start: 26571
• Page End: 26576
• Publication Date: 2021-11-09
• Subjects: germylation -- nickel -- organogermanes -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202112876
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Cross‐electrophile coupling has emerged as a promising tool for molecular synthesis; however, current studies have focused mainly on forging C−C bonds. We report a cross‐electrophile C−Ge coupling reaction and thereby demonstrate the possibility of constructing organogermanes from carbon electrophiles and chlorogermanes. The reaction proceeds under mild conditions and offers access to both aryl and alkenyl germanes. Electron‐rich, electron‐poor, and ortho ‐/ meta ‐/ para ‐substituted (hetero)aryl electrophiles, as well as cyclic and acyclic alkenyl electrophiles, were coupled. Gram‐scale reaction, incorporation of the ‐GeR3 moiety into complex biologically active molecules, and derivatization of formed organogermanes are demonstrated. Abstract : A new C−Ge bond‐forming framework was established, which bridges a gap between a recently developed mild coupling technique and organogermane chemistry. The method provides a mild approach for the synthesis of both aryl and alkenyl germanes, with improved molecular diversity and structural complexity, using readily available carbon electrophiles and chlorogermanes as starting materials.