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![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Synthesis of Densely Functionalized Pyrroles via Photoinduced C-Insertion into N-Alkylenamines: Sequential
Chuan-Hua Qu1, Su-Ya Liu1, Shan-Shan Chen1
1International Academy of Targeted Therapeutics and Innovation, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing 402160, China.
Abstract:
Photoinduced Csp3-Br bond homolysis of ArCOCF2Br using triethylamine as the halogen bonding (XB) acceptor was a key step for the [2 + 2 + 1] cyclization. An unprecedented strategy for assembling privileged pyrroles and their fused scaffolds via metal-, oxidant-free C-incorporation into N-alkylenamines through a triple-cleavage process has been disclosed. This method uses readily available alkyl amines, alkynes, or CF3-containing N-benzylenamines as the starting material and features two consecutive C-C-forming reactions with ArCOCF2Br as the carbon source. The transformation exploits the dual reactivity of bromine radicals─hydrogen-atom transfer (HAT) and reversible radical addition (RRA)─to coactivate the N-alkylenamines, and the resulting open-shell intermediates are then intercepted by in situ-generated difluoroalkyl radicals to deliver the target heterocycles.
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