Journal
SYNLETT
Volume 32, Issue 4, Pages 406-410Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1319-6237
Keywords
hydroacylation; ketones; eosin Y; hydrogen atom transfer; acyl radicals; photocatalysis
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Funding
- Ministry of Education (MOE) of Singapore [MOE2017-T2-2081]
- National Natural Science Foundation of China [21871205, 22071170]
- National University of Singapore (Suzhou) Research Institute
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Styrene derivatives were hydroacylated with exclusive anti-Markovnikov selectivity using neutral eosin Y as a direct hydrogen-atom-transfer catalyst under visible-light irradiation, giving moderate to high yields of the corresponding products. The acyl radical intermediate was generated through a direct HAT process induced by photoexcited eosin Y, followed by subsequent addition to styrenes and a reverse HAT process to generate the ketone products.
Styrene derivatives were hydroacylated with exclusive anti-Markovnikov selectivity by using neutral eosin Y as a direct hydrogen-atom-transfer (HAT) catalyst under visible-light irradiation. Aldehydes and styrenes with various substituents were tolerated (>20 examples), giving the corresponding products in moderate to high yields. The key acyl radical intermediate was generated from a direct HAT process induced by photoexcited eosin Y. Subsequent addition to styrenes and a reverse HAT process generated the ketone products.
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