Utilization of Borane-Catalyzed Hydrosilylation as a Dearomatizing Tool: Six-Membered Cyclic Amidine Synthesis from Isoquinolines and Pyridines

Abstract

In this study, a convenient strategy to synthesize six-membered­ cyclic amidines from isoquinolines and pyridines has been developed. Borane-catalyzed hydrosilylation of each N-heteroarene was utilized as a dearomatizing tool. Substrate scope is broad with respect to both isoquinolines and pyridines, with various reaction pathways depending on the substitution pattern of the N-heteroarenes. The reaction mechanism and reactivity of each class of N-heteroarenes has been discussed. The resulting six-membered (Z)-sulfonyl amidine products are rarely reported and are mostly unprecedented. The scalability of this method and versatility of the cyclic amidine products are also presented.

Key words

cyclic amidine - hydrosilylation - N-heteroarenes - dearomatization - [3+2] cycloaddition - B(C₆F₅)₃

Publication History

Received: 18 August 2020

Accepted after revision: 09 September 2020

Article published online:
12 October 2020

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