We report a novel method for the chlorothiolation of alkenes using HCl and sulfoxides to achieve the 1,2-difunctionalization of unactivated alkenes. The combination of our new HCl reagent (HCl/DMPU) with sulfoxides forms a unique chlorothiolation system. Both terminal and internal alkenes are suitable substrates. This method works at gram scale and is applicable in further synthetic elaborations.
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http://dx.doi.org/10.1002/ejoc.201800973 | DOI Listing |
J Org Chem
January 2020
School of Chemical Engineering , Nanjing University of Science and Technology, Nanjing 210094 , P. R. China.
Newly developed sulfonyl chloride-based regioselective chlorothiolation of alkenes has been disclosed; the reaction is compatible with a variety of functional groups and can be scaled up to the gram scale with no loss in yield. The employment of readily available reactants, mild reaction conditions, and high regioselectivity makes this process very practical. Mechanistic studies revealed a possible free radical reaction pathway.
View Article and Find Full Text PDFEuropean J Org Chem
September 2018
College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, China.
We report a novel method for the chlorothiolation of alkenes using HCl and sulfoxides to achieve the 1,2-difunctionalization of unactivated alkenes. The combination of our new HCl reagent (HCl/DMPU) with sulfoxides forms a unique chlorothiolation system. Both terminal and internal alkenes are suitable substrates.
View Article and Find Full Text PDFOrg Lett
November 2018
School of Chemical Engineering , Nanjing University of Science and Technology, Nanjing 210094 , P. R. China.
A copper-catalyzed vicinal chloro-thiolation of alkynes with inexpensive and diversified sulfonyl chlorides RSOCl (R = aryl, alkyl) has been developed. This practical and scalable reaction could be used for the construction of a number of unexplored bioactive chlorothiolated alkenes. Internal alkynes could also undergo the chloro-thiolation to provide tetrasubstituted alkynes.
View Article and Find Full Text PDFChem Rec
August 2016
Research Institute for Interdisciplinary Science, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.
Multisubstituted olefins are fundamental motifs in organic compounds. In this account, we describe the synthesis of organic molecules bearing an olefinic moiety by the transition-metal-catalyzed regio- and stereoselective addition of a variety of interelement compounds to alkynes. Regio- and stereoselective silaboration, diborylation, and chlorothiolation have been achieved by using the transition-metal catalysts.
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