Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N-(Acyloxy)phthalimides at Room Temperature

Guang-Zu Wang, Rui Shang* and Yao Fu*

*School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; University of Science and Technology of China, Hefei 230026, China, Email: ruichem.s.u-tokyo.ac.jp, fuyaoustc.edu.cn

G.-Z. Wang, R. Shang, Y. Fu, Org. Lett., 2018, 20, 888-891.

DOI: 10.1021/acs.orglett.8b00023

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Abstract

The combination of Pd(PPh₃)₂Cl₂ with Xantphos efficiently catalyzes a decarboxylative Heck reaction of vinyl arenes and vinyl heteroarenes with aliphatic N-(acyloxy)phthalimides under irradiation of blue LEDs at room temperature. A broad scope of secondary, tertiary, and quaternary carboxylates, including α-amino acid derived esters, can be converted with high stereoselectivity.

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Key Words

Heck reaction, alkenylation, cyclohexanes, photochemistry

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ID: J54-Y2018