Direct Substitution of Secondary and Tertiary Alcohols To Generate Sulfones under Catalyst- and Additive-Free Conditions

Yanan Liu; Peizhong Xie; Zuolian Sun; Xiangyang Wo; Cuiqing Gao; Weishan Fu; Teck-Peng Loh

doi:10.1021/acs.orglett.8b02188

Direct Substitution of Secondary and Tertiary Alcohols To Generate Sulfones under Catalyst- and Additive-Free Conditions

Org Lett. 2018 Sep 7;20(17):5353-5356. doi: 10.1021/acs.orglett.8b02188. Epub 2018 Aug 14.

Authors

Yanan Liu¹, Peizhong Xie¹, Zuolian Sun¹, Xiangyang Wo¹, Cuiqing Gao², Weishan Fu¹, Teck-Peng Loh^{1

3}

Affiliations

¹ School of Chemistry and Molecular Engineering, Institute of Advanced Synthesis, Jiangsu National Synergetic Innovation Center for Advanced Materials , Nanjing Tech University , Nanjing 211816 , China.
² Southern Modern Forestry Collaborative Innovation Center, College of Forestry , Nanjing Forestry University , Nanjing 210037 , China.
³ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences , Nanyang Technological University , Singapore 637371.

PMID: 30106300
DOI: 10.1021/acs.orglett.8b02188

Abstract

An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.

Publication types

Research Support, Non-U.S. Gov't