Synthesis 2017; 49(21): 4753-4758
DOI: 10.1055/s-0036-1588811
special topic
© Georg Thieme Verlag Stuttgart · New York

NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl Boronates

Won Jun Jang, Jung Tae Han, Jaesook Yun*
  • Department of Chemistry and Institute of Basic Science, Sungkyunkwan University, Suwon 16419, Korea   Email: jaesook@skku.edu
Supported by: National Research Foundation of Korea grant (NRF-2016R1A2B4011719) funded by the Korean government (MEST).
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Publication History

Received: 03 March 2017

Accepted after revision: 04 April 2017

Publication Date:
03 May 2017 (eFirst)

Published as part of the Special Topic Modern Strategies for Borylation in Synthesis

Abstract

A tandem hydrocupration/allylation of alkenyl boronates efficiently proceeds with NHC-copper catalysts using hydrosilane and allyl phosphate as reagents. In the presence of IMes–Cu catalyst, the allylation of in situ generated Β-α-copper intermediates smoothly occurs to give homoallylic boronates in high yields, despite competitive side reaction pathways. Mono- and disubstituted alkenyl boronates were effective in the reaction with terminal allyl phosphates, but trisubstituted substrates showed limited reactivity.

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