Towards a Step-Economical and Waste-Free [hmim]Br-Catalyzed Deprotection of -Sulfido Carbonyl Groups into (E)-Enones and Mechanistic Insights

A neutral ionic liquid, [hmim]Br, catalyzed the direct dehydrosulfenylation of -sulfido carbonyl compounds under microwave irradiation into the corresponding ,-unsaturated compounds with exclusive trans selectivity in one pot. This procedure improves on conventional routes, which require an addition...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 6; no. 12; pp. 1867 - 1875
Main Authors Thopate, Yogesh, Singh, Richa, Sharma, Tanuj, Siddiqi, Mohammad I., Sinha, Arun K.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.12.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
dehydrosulfenylation
ORGANIC-SYNTHESIS
PROTECTION
IONIC-LIQUID
AMBIPHILIC CHARACTER
reaction mechanisms
ELIMINATION
density functional calculations
KETONES
THIOL
microwave chemistry
METAL
ionic liquids
IN-SITU
CONJUGATE ADDITION
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Summary:A neutral ionic liquid, [hmim]Br, catalyzed the direct dehydrosulfenylation of -sulfido carbonyl compounds under microwave irradiation into the corresponding ,-unsaturated compounds with exclusive trans selectivity in one pot. This procedure improves on conventional routes, which require an additional step for oxidation of the -sulfido carbonyl compounds into the corresponding sulfoxides/sulfones prior to the dehydrosulfenylation step in the presence of a metal catalyst/oxidant or a base/acid catalyst. Notably, this step-economical and waste-free dehydrosulfenylation procedure has also been extended to the generation of (E)-dienes from -hydroxy sulfido compounds through a tandem dehydrosulfenylation/dehydration process in [hmim]Br. Moreover, (HNMR)-H-1, MS (DART), and DFT studies provided insight into the progress and mechanism of this reaction, and revealed the crucial role of [hmim]Br in promoting the dehydrosulfenylation step, which, alongside the possible recyclability of [hmim]Br, make this procedure environmentally desirable.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201700409