Zinc(II)-Catalyzed Redox Cross-Dehydrogenative Coupling of Propargylic Amines and Terminal Alkynes for Synthesis of N-Tethered 1,6-Enynes

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Zinc(II)-Catalyzed Redox Cross-Dehydrogenative Coupling of Propargylic Amines and Terminal Alkynes for Synthesis of N-Tethered 1,6-Enynes

Sugiishi, Tsuyuka; Nakamura, Hiroyuki

Journal of the American Chemical Society, 02/2012, Volume: 134, Issue: 5

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The zinc(II)-catalyzed redox cross-dehydrogenative coupling (CDC) of propargylic amines and terminal alkynes proceeds to afford N-tethered 1,6-enynes. In the current CDC reaction, a C(sp)–C(sp3) bond is formed between the carbon adjacent to the nitrogen atom in the propargylic amine and the terminal carbon of the alkyne with reduction of the C–C triple bond of the propargylic amine, which acts as an internal oxidant.

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