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Synthesis 2015; 47(11): 1669-1677
DOI: 10.1055/s-0034-1380384
DOI: 10.1055/s-0034-1380384
paper
Trifluoroborane-Catalyzed C–H Functionalization/S–H Insertion Reaction: Construction of N,S-Acetal Quaternary Centers
Further Information
Publication History
Received: 31 October 2014
Accepted after revision: 19 February 2015
Publication Date:
25 March 2015 (online)
Abstract
The trifluoroborane-catalyzed C–H functionalization/S–H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.
Key words
α-diazophosphonate - C–H functionalization - S–H insertion - N,S-acetal - combined reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380384.
- Supporting Information
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For selected recent examples, see:
For selected epidithiodiketopiperazine total syntheses, see ref. 1a and:
For selected examples, see:
For selected recent examples, see:
For recent reviews, see:
For elected examples on carbenoid C–H insertion, see ref. 7d and:
For selected examples on carbenoid O–H insertion, see:
For selected examples on carbenoid N–H insertion, see:
For selected examples on carbenoid Si–H insertion, see:
For metallo-carbene insertion into N–H bonds, see:
For metallo-carbene insertion into O–H bonds, see:
For recent reviews see the following: