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Useful intermediates: Addition of silyl-substituted chloroalkynes to terminal alkynes, namely chloroalkynylation, proceeds under palladium catalysis to afford (Z)-1-chloro-1,3-enynes (see scheme). The carbon–chlorine bond of the adducts is easily convertible to a carbon–carbon bond by using palladium-catalyzed cross-coupling reactions to provide a variety of 1,3-enynes.
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Wada et al. (2010) studied this question.
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