Multicomponent Cyclization with an Inorganic Sulfur Dioxide Surrogate: Straightforward Construction of Difluorinated Benzosultams

Yu-Heng Wu; Cheng-Jing Li; Zhong-Lin Wei; Wei-Wei Liao

doi:10.1021/acs.orglett.2c03771

Multicomponent Cyclization with an Inorganic Sulfur Dioxide Surrogate: Straightforward Construction of Difluorinated Benzosultams

Org Lett. 2022 Dec 16;24(49):9112-9117. doi: 10.1021/acs.orglett.2c03771. Epub 2022 Dec 1.

Authors

Yu-Heng Wu¹, Cheng-Jing Li¹, Zhong-Lin Wei¹, Wei-Wei Liao^{1

2}

Affiliations

¹ Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P R China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P R China.

PMID: 36453929
DOI: 10.1021/acs.orglett.2c03771

Abstract

A straightforward three-component transformation for the preparation of functionalized benzosultams under TM-free and mild reaction conditions was described, in which easy-to-handle Na₂S₂O₅, available bromodifluoroalkyl reagent, and N-(2-haloaryl) cyanamide were employed. Na₂S₂O₅ was essential to the generation of difluoroalkyl radical, SO₂ fixation, and cyclization, which enabled efficient construction of target products in a sustainable manner. A broad substrate scope and modular feature made this protocol attractive for exploring the chemical space of the construction of cyclic sulfonamides.