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A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C-C Bond Scission

Neil J. McAlpine, Long Wang, Brad P. Carrow*

*Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States, Email:

N. J. McAlpine, L. Wang, B. P. Carrow, J. Am. Chem. Soc., 2018, 140, 13634-13639.

DOI: 10.1021/jacs.8b10007


An aerobic boron Heck reaction with cyclobutene forms exclusively linear 1-aryl-1,3-dienes using (hetero)arylboronic acids, or 1,3,5-trienes using alkenylboronic acids, rather than typical Heck products (i.e., substituted cyclobutenes).

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Key Words

Heck Reaction, Oxygen, Alkenylation of Arenes, Dienes

ID: J48-Y2018