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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
Rhodium(III)-Catalyzed Triple Aryl/Alkenyl C-H Bond Activation of Aryl Enaminones to Access Naphtho[1,8-bc]pyrans
Yunlong Li1,2, Wenchao Jiang1,2, Jie Lin1,2
1Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. China.
Abstract:
Rhodium(III)-catalyzed triple C-H bond activation of aryl enaminones was achieved to access naphtho[1,8-bc]pyrans by oxidative annulation to internal alkynes. 1-Naphthols might be formed as the only products, depending on the steric and/or electronic environment around the aroyl moiety of the aryl enaminones or the electronic impact from the alkynes. With propargyl alcohols as the masked terminal alkynes, aryl enaminones underwent rhodium(III)- or rhodium(I)-catalyzed internal alkenyl C-H bond activation to afford functionalized but-2-ene-1,4-diones. The resultant naphtho[1,8-bc]pyrans are highly fluorescent and can be further transformed by chlorination, bromination, and difluoromethylation, demonstrating potential practicability of the synthetic protocol.
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