Silver-mediated oxidative trifluoromethylthiolation of cycloalkanols by C-C bond cleavage: a regioselective approach to distally trifluoromethylthiolated ketones

A novel method for the oxidative trifluoromethylthiolation of cycloalkanols by AgSCF 3 /K 2 S 2 O 8 is described. The methodology provides an efficient and regioselective approach to distally trifluoromethylthiolated ketones in moderate to good yields. The reaction that is easily handled has a good...

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Published inRSC advances Vol. 6; no. 58; pp. 5271 - 52714
Main Authors Huang, Feng-Qing, Wang, Yue-Wei, Sun, Jian-Guo, Xie, Jian, Qi, Lian-Wen, Zhang, Bo
Format Journal Article
LanguageEnglish
Published 01.01.2016
Subjects
chemical bonding
cleavage (chemistry)
ketones
regioselectivity
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ISSN2046-2069
2046-2069
DOI10.1039/c6ra11968a

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Summary:A novel method for the oxidative trifluoromethylthiolation of cycloalkanols by AgSCF 3 /K 2 S 2 O 8 is described. The methodology provides an efficient and regioselective approach to distally trifluoromethylthiolated ketones in moderate to good yields. The reaction that is easily handled has a good functional-group tolerance and broad scope. Initial mechanistic studies indicate that the reaction may proceed via a radical pathway involving a tandem C(sp 3 )-C(sp 3 ) bond cleavage and C(sp 3 )-SCF 3 bond formation process. Various distally trifluoromethylthiolated ketones were readily prepared by silver-mediated oxidative trifluoromethylthiolation of cycloalkanols. The reaction features complete regioselectivity, operational simplicity, and excellent practicality.
Bibliography:Electronic supplementary information (ESI) available: Experimental details and characterization data for the products. See DOI
10.1039/c6ra11968a
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:2046-2069
2046-2069
DOI:10.1039/c6ra11968a