Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature

Guang-Zu Wang, Rui Shang*, Wan-Min Cheng and Yao Fu*

*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, W.-M. Cheng, Y. Fu, J. Am. Chem. Soc., 2017, 139, 18307-18312.

DOI: 10.1021/jacs.7b10009

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Abstract

A palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. Probably, a photoexcited-state reactivity of the palladium complex enhances oxidative addition and suppresses undesired β-hydride elimination.

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Key Words

Heck reaction, alkenes, photochemistry

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ID: J48-Y2017