We report the gold-catalyzed reaction of vinyldiazo compounds and alkenylsilanes to produce skipped dienes, which are common structural motifs in an array of bioactive compounds. This carbon-carbon bond-forming transformation proceeds with complete regio- and stereoselectivity with the silyl group serving as a regio- and stereocontrolling element. Likewise, the use of alkynylsilanes as reaction partners yielded skipped enynes resulting from a C(sp)-C(sp) coupling. Mechanistic experiments and DFT studies have provided support for a stepwise mechanism.
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| http://dx.doi.org/10.1021/acs.orglett.1c01381 | DOI Listing |
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