Iodine-Mediated Direct Generation of o-Quinone Methides at Room Temperature: A Facile Protocol for the Synthesis of ortho-Hydroxybenzyl Thioethers

R Sidick Basha; Chia-Wei Chen; Daggula Mallikarjuna Reddy; Chin-Fa Lee

doi:10.1002/asia.201800233

Iodine-Mediated Direct Generation of o-Quinone Methides at Room Temperature: A Facile Protocol for the Synthesis of ortho-Hydroxybenzyl Thioethers

Chem Asian J. 2018 Sep 4;13(17):2475-2483. doi: 10.1002/asia.201800233. Epub 2018 May 14.

Authors

R Sidick Basha¹, Chia-Wei Chen¹, Daggula Mallikarjuna Reddy¹, Chin-Fa Lee^{1

2

3}

Affiliations

¹ Department of Chemistry, National Chung Hsing University (NCHU), Taichung, Taiwan, 402, R.O.C.
² Research Center for Sustainable Energy and Nanotechnology, (NCHU), Taichung, Taiwan, 402, R.O.C.
³ Innovation and Development Center of Sustainable Agriculture, (NCHU), Taichung, Taiwan, 402, R.O.C.

PMID: 29624908
DOI: 10.1002/asia.201800233

Abstract

An iodine-mediated preparation of ortho-quinone methides (o-QMs) from ortho-hydroxybenzyl alcohols by a C-O bond scission strategy is described. The in situ generated o-QMs were then employed for C-S bond formation by thio-Michael addition of thiols to provide the ortho-hydroxybenzyl thioethers (o-HBT) in moderate to excellent yields.

Keywords: 2-hydroxymethyl-substituted phenol; Michael reaction; iodine; ortho-quinone methide; thioether.