The
susceptibility of gold phosphito compounds to undergo alkyne
insertion into gold–phosphorus bonds has been investigated.
An electron-deficient alkyne (DMAD) underwent syn-insertion into the gold–phosphorus bond to generate a Z-vinylgold species, whereas electron-rich internal alkynes
were unreactive. When a P-chiral phosphinate was used as a probe,
the protodeauration and insertion steps were found to be stereospecific.
In contrast to the insertion chemistry observed with DMAD, electron-deficient
terminal alkynes generated alkynylgold compounds and released secondary
phosphites through a reversible protodeauration process.
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