Synthesis of highly substituted N-(furan-3-ylmethylene)benzenesulfonamides by a gold(I)-catalyzed oxidation/1,2-alkynyl migration/cyclization cascade

Tao Wang; Long Huang; Shuai Shi; Matthias Rudolph; A Stephen K Hashmi

doi:10.1002/chem.201404229

Synthesis of highly substituted N-(furan-3-ylmethylene)benzenesulfonamides by a gold(I)-catalyzed oxidation/1,2-alkynyl migration/cyclization cascade

Chemistry. 2014 Nov 3;20(45):14868-71. doi: 10.1002/chem.201404229. Epub 2014 Sep 18.

Authors

Tao Wang¹, Long Huang, Shuai Shi, Matthias Rudolph, A Stephen K Hashmi

Affiliation

¹ Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-54-4205.

PMID: 25236914
DOI: 10.1002/chem.201404229

Abstract

A variety of N-(furan-3-ylmethylene)benzenesulfonamides were obtained by a gold(I)-catalyzed cascade reaction from easily accessible starting materials. The reaction pathway involves a rarely observed 1,2-alkynyl migration onto a gold carbenoid. This observation further enriches gold carbenoid chemistry with regard to group migration.

Keywords: alkynes; furans; gold catalysis; imines; sulfonamides.