KOtBu-Promoted, Three-Component Domino Reaction of Arenes(indoles/phenols), C60, and (Per/poly)fluoroarenes: Achieving Direct C-C Cross-Coupling of Fullerene with (Per/poly)fluoroarenes

Jun-Xiang Zhang; Ming-Wei Liu; Wan-Yu Wang; Rui-Lin Jia; Man-Qing Yan; Jun Xuan; Fei Li

doi:10.1021/acs.joc.2c01912

KO^tBu-Promoted, Three-Component Domino Reaction of Arenes(indoles/phenols), C₆₀, and (Per/poly)fluoroarenes: Achieving Direct C-C Cross-Coupling of Fullerene with (Per/poly)fluoroarenes

J Org Chem. 2023 Jan 6;88(1):116-131. doi: 10.1021/acs.joc.2c01912. Epub 2022 Dec 20.

Authors

Jun-Xiang Zhang¹, Ming-Wei Liu¹, Wan-Yu Wang¹, Rui-Lin Jia¹, Man-Qing Yan¹, Jun Xuan¹, Fei Li^{1

2}

Affiliations

¹ Department of Chemistry, Anhui University, Hefei, Anhui 230601, China.
² Key Laboratory of Structure and Functional Regulation of Hybrid Materials (Anhui University), Ministry of Education; Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials and Key Laboratory of Functional Inorganic Materials of Anhui Province, Hefei, Anhui 230601, China.

PMID: 36538325
DOI: 10.1021/acs.joc.2c01912

Abstract

A KO^tBu-promoted, three-component cross-coupling of arenes(indoles/phenols), C₆₀, and (per/poly)fluoroarenes has been established for the one-pot efficient synthesis of various 1,4-arene-bridged bis(polyfluoroaryl)-functionalized [60]fullerenes. This developed reaction system demonstrates good functional group compatibilities with broad substrate scope, which exhibits high regio- and chemoselectivities. Further control experiment succeeded in providing a one-pot protocol for the synthesis of various 1,2-N-(per/poly)fluoroarene-substituted 1,2-(3-indole)(hydro)fullerenes.