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Fe-Catalyzed Reductive Couplings of Terminal (Hetero)Aryl Alkenes and Alkyl Halides under Aqueous Micellar Conditions

Haobo Pang, Ye Wang, Fabrice Gallou and Bruce H. Lipshutz*

*Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States, Email:

H. Pang, Y. Wang, F. Gallou, B. H. Lipshutz, J. Am. Chem. Soc., 2019, 141, 17117-17124.

DOI: 10.1021/jacs.9b09336

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A reductive coupling of a vinyl-substituted aromatic or heteroaromatic and an alkyl bromide or iodide occurs in an aqueous micellar medium in the presence of Zn and a catalytic amount of an Fe(II) salt at rt. The new C-C bond is regiospecifically formed at rt at the β-site of the alkene via a radical process.

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Key Words

C-C coupling, Zn

ID: J48-Y2019