Visible-Light-Promoted Ring-Opening Alkynylation, Alkenylation, and Allylation of Cyclic Hemiacetals through β-Scission of Alkoxy Radicals

Jiang-Ling Shi; Zixuan Wang; Rui Zhang; Yuankai Wang; Jianbo Wang

doi:10.1002/chem.201901762

Visible-Light-Promoted Ring-Opening Alkynylation, Alkenylation, and Allylation of Cyclic Hemiacetals through β-Scission of Alkoxy Radicals

Chemistry. 2019 Jul 5;25(38):8992-8995. doi: 10.1002/chem.201901762. Epub 2019 Jun 6.

Authors

Jiang-Ling Shi¹, Zixuan Wang¹, Rui Zhang¹, Yuankai Wang¹, Jianbo Wang^{1

2}

Affiliations

¹ Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory, of Bioorganic Chemistry and Molecular Engineering of, Ministry of Education, College of Chemistry, Peking University, Beijing, 100871, China.
² The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China.

PMID: 31066949
DOI: 10.1002/chem.201901762

Abstract

The alkoxy radicals that are derived from cyclic hemiacetals have been generated through the visible-light-promoted reaction of the corresponding N-alkoxyphthalimides with Hantzsch ester as the reductant. The alkoxy radicals subsequently undergo β-scission of the C-C bond to generate carbon-centered radicals, which are trapped by alkynyl-, alkenyl-, or allylsulfones.

Keywords: alkoxy radicals; beta-scission; cyclic hemiacetal; ring-opening reactions; visible-light irradiation.

Abstract

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