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Synthesis 2017; 49(21): 4753-4758
DOI: 10.1055/s-0036-1588811
DOI: 10.1055/s-0036-1588811
special topic
NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl Boronates
Supported by: National Research Foundation of Korea grant (NRF-2016R1A2B4011719) funded by the Korean government (MEST).Further Information
Publication History
Received: 03 March 2017
Accepted after revision: 04 April 2017
Publication Date:
03 May 2017 (online)
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.
Key words
allylic substitution - copper - homoallylic boronates - hydrocupration - N-heterocyclic carbenes - tandem reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588811.
- Supporting Information
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