Visible-light-induced direct perfluoroalkylation/heteroarylation of [1.1.1]propellane to diverse bicyclo[1.1.1]pentanes (BCPs) under metal and photocatalyst-free conditions?

Green Chemistry Pub Date: 2023-01-12 DOI: 10.1039/D2GC04521D

Abstract

Herein, a green and novel multi-component reaction for direct perfluoroalkylation/heteroarylation of [1.1.1]propellane with heteroarenes and perfluoroalkyl iodines has been described. This transformation is facilitated by visible light in the absence of any transition-metal catalysts and photocatalysts. Various heteroarenes and perfluoroalkyl iodines are well compatible, providing the corresponding products in moderate-to-good yields. The control experiments demonstrate that a radical-relay mechanism is responsible for the cascade reaction. Such a methodology offers an efficient and practical access to diverse 1-perfluoroalkyl-3-heteroaryl bicyclo[1.1.1]pentanes (BCPs) with the potential for various applications in organic synthesis.

Graphical abstract: Visible-light-induced direct perfluoroalkylation/heteroarylation of [1.1.1]propellane to diverse bicyclo[1.1.1]pentanes (BCPs) under metal and photocatalyst-free conditions
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