Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 15, Pages 10098-10109Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01355
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Funding
- Science and Engineering Research Board, New Delhi [SERB/EMR/2015/002482]
- Council of Scientific and Industrial Research, New Delhi [02(0263)/16/EMR-II]
- DST-PURSE, New Delhi
- UGC, New Delhi
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A metal- and oxidant-free photoinduced strategy for thioxo sulfur-selective trifluoromethylation of beta-ketodithioesters at room temperature is reported. Excellent Z/E-stereoselectivity has been achieved with cheap and viable Langlois' reagent (CF3SO2Na, sodium triflinate) in the presence of eosin Y, which acts as a hydrogen atom transfer (HAT) catalyst. The reaction proceeds via disulfide intermediate disulfanediylbis(3-(alkylthio)-1-phenylprop-2-en-1-one) (a dimer of beta-ketodithioester) followed by complementing proton-coupled electron transfer-mediated reverse HAT cycle of eosin Y. This operationally simple and efficient protocol allows direct access to triflinated alpha-oxoketene dithioacetals in good to excellent yields bearing diverse synthetically useful functional groups of different electronic and steric nature.
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