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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Reductive Dechlorination of Aryl Chlorides Using Hantzsch Ester
Haitao Wang1,2, Zesheng Li1,2, Han-Yuan Liu1,2
1Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
None:
Herein, we report a transition-metal-free reductive dechlorination of aryl and alkyl chlorides using Hantzsch ester as the sole reductant. Operating under 365 nm UV irradiation or at 100 °C temperature, this method represents a significant simplification without the need for additional catalysts or inert protection. It exhibits excellent chemoselectivity, with reduction-sensitive functional groups, such as esters, aldehydes, and ketones, left completely intact. Mechanistic studies and DFT calculations reveal divergent mechanisms: a concerted SNAr pathway under thermal conditions while a single-electron transfer (SET) pathway under photochemical conditions.
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