Photo-mediated selective deconstructive geminal dihalogenation of trisubstituted alkenes

Han Wang, Ren Wei Toh, Xiangcheng Shi, Tonglin Wang, Xu Cong and Jie Wu ()
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Han Wang: National University of Singapore
Ren Wei Toh: National University of Singapore
Xiangcheng Shi: National University of Singapore
Tonglin Wang: Northwest Normal University
Xu Cong: National University of Singapore
Jie Wu: National University of Singapore

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Selective deconstructive functionalization of alkenes, other than the well-established olefin metathesis and ozonolysis, to produce densely functionalized molecular scaffolds is highly attractive but challenging. Here we report an efficient photo-mediated deconstructive germinal dihalogenation of carbon-carbon double bonds. A wide range of geminal diiodoalkanes and bromo(iodo)alkanes (>40 examples) are directly prepared from various trisubstituted alkenes, including both cyclic and acyclic olefins. This C=C cleavage is highly chemoselective and produces geminal dihalide ketones in good yields. Mechanistic investigations suggest a formation of alkyl hypoiodites from benzyl alcohols and N-iodoimides, which undergo light-induced homolytic cleavage to generate active oxygen radical species.

Date: 2020
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DOI: 10.1038/s41467-020-18274-2

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