Synthesis 2017; 49(22): 5007-5016
DOI: 10.1055/s-0036-1588501
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Regio- and Stereoselective Hydrosulfonation of Propiolate Esters

Selvam Rajua, Pratheepkumar Annamalaia, Fu-Wei Chana, Po-Yen Tsenga, Po-Yen Chena, Ting-Shen Kuob, Shih-Ching Chuang*a
  • aDepartment of Applied Chemistry, National Chiao Tung University, Hsinchu 30010, Taiwan, R.O.C.
  • bDepartment of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan, R.O.C.   Email: jscchuang@faculty.nctu.edu.tw
Ministry of Science and Technology of Taiwan (MOST104-2113-M-009-014-MY3 and MOST105-2628-M-009-002-MY3)
Further Information

Publication History

Received: 15 April 2017

Accepted after revision: 09 June 2017

Publication Date:
31 July 2017 (eFirst)

Abstract

An efficient palladium-catalyzed addition reaction of alkyl- and arylsulfonic acids to propiolate esters to yield alkenyl sulfonates is demonstrated. The formation of alkenyl sulfonates is highly regio- and stereoselective with favorable yields of up to 95%, and two of the alkenyl sulfonates are utilized for a Sonogashira cross-coupling reaction to produce (Z)-1,3-enynoates.

Supporting Information

 
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