Cs2CO3-Mediated Regio- and Stereoselective Sulfonylation of 1,1-Dibromo-1-alkenes with Sodium Sulfinates-Reference-Cited by-同舟云学术

Cs2CO3-Mediated Regio- and Stereoselective Sulfonylation of 1,1-Dibromo-1-alkenes with Sodium Sulfinates

Published:2020-10-06 Issue:06 Volume:53 Page:1149-1156
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Shiri Morteza¹^ORCID,Salehi Parvin¹,Mohammadpour Zeinab¹,Salehi Peyman²^ORCID,Notash Behrouz³

Affiliation:

1. Department of Chemistry, Faculty of Physics and Chemistry, Alzahra University

2. Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University

3. Department of Chemistry, Shahid Beheshti University

Abstract

AbstractA highly selective synthesis of (Z)-1-bromo-1-sulfonyl alkenes via Cs2CO3-promoted sulfonylation of 1,1-dibromo-1-alkenes with sodium sulfinates is described. Notably, using excess amounts of Cs2CO3 and sodium sulfinate in such a reaction regenerated the parent aldehyde. Interestingly, the reaction of 1-(2,2-dibromovinyl)-2-nitrobenzene in the presence of sulfinates and Cs2CO3 produced isatin. The Sonogashira cross coupling of synthesized (Z)-1-bromo-1-sulfonyl alkenes with phenylacetylene gave selectively the corresponding sulfonylalkynyl alkenes.

Funder

Alzahra University

Iran National Science Foundation

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1706295.pdf

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