Geometrically Compelled Silicon(II)/Silicon(IV) Donor–Acceptor Interaction Enables the Enamination of Nitriles

Author:

Kong Deliang1,Li Jiancheng1ORCID,Dai Wen1,Jiang Liuying1ORCID,Zhao Yiling1ORCID,Zhu Hongping1ORCID,Fu Gang1,Roesky Herbert W.2ORCID

Affiliation:

1. State Key Laboratory of Physical Chemistry of Solid Surface, College of Chemistry and Chemical Engineering Xiamen University Xiamen, Fujian 361005 China

2. Institüt für Anorganische Chemie Universität Göttingen Tammannstraße 4 37077 Göttingen Germany

Abstract

AbstractDiscovering new bonding scenarios and subsequently exploring the reactivity contribute substantially to advance the main group element chemistry. Herein, we report on the isolation and characterization of an intriguing class of the hydrido‐benzosiloles 24. These compounds exhibit a side arm of the amidinatosilylenyl group, featuring unidirectional silicon(II)/silicon(IV) donor‐acceptor interaction on account of the geometric constraint. Furthermore, the reactions involving 24 with nitriles yield the tricyclic compounds that edge‐fused of the Si‐heteroimidazolidine‐CN2Si2, silole‐C4Si, and phenyl‐C6‐rings (513). These compounds are manifesting a unique reaction that the silicon(II)/silicon(IV) interaction enables the enamination of the α‐H‐bearing nitriles. The reaction mechanism involved in H‐shift under oxidative addition at silylene followed by hydrosilylation of a ketenimine intermediate was revealed by density function theory (DFT) calculations.

Funder

National Science and Technology Program during the Twelfth Five-year Plan Period

Publisher

Wiley

Subject

General Chemistry,Catalysis

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