Tetrahedron Letters p. 1855 - 1858 (1991)
Update date:2022-08-16
Topics:
Rozema, Michael J.
Knochel, Paul
The reaction of alkynylcoppers 1 with an excess of iodomethylzinc iodide selectively furnishes the quadruple methylene insertion copper organometallics 2 in fair to good yields. The mechanism of the reaction has been investigated and postulated intermediates such as 4 or 8 have been trapped with electrophiles like aldehydes or ketones in excellent yields. A new in situ preparation of propargylic copper derivatives 4 starting from readily available alkynylcopper compounds has been developed leading to homopropargylic alcohols in 80-95% yield.
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