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Synthesis 2021; 53(04): 754-764
DOI: 10.1055/s-0040-1707323
DOI: 10.1055/s-0040-1707323
paper
Utilization of Borane-Catalyzed Hydrosilylation as a Dearomatizing Tool: Six-Membered Cyclic Amidine Synthesis from Isoquinolines and Pyridines
This research was supported by the National Research Foundation of Korea (NRF-2018R1D1A1B07045397) and Korea Basic Science Institute (KBSI) National Research Facilities & Equipment Center (NFEC) grant funded by the Korea government (Ministry of Education) (no. 2019R1A6C1010005). This work was carried out by the convergence Research Laboratory established by the Mokpo National University (MNU) Innovation Support Project.
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)3Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707323.
- Supporting Information
Publication History
Received: 18 August 2020
Accepted after revision: 09 September 2020
Article published online:
12 October 2020
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