Syn-Insertion of Alkynes into Gold–Phosphito Bonds: Stereoselectivity and Reversible Protodeauration,Organometallics

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Syn-Insertion of Alkynes into Gold–Phosphito Bonds: Stereoselectivity and Reversible Protodeauration
Organometallics ( IF 2.5 ) Pub Date : 2021-07-05 , DOI: 10.1021/acs.organomet.1c00283
Carly L. Masonheimer ₁ , Madeleine G. Atwood ₁ , Susan E. Hartzell ₁ , Erin A. Reph ₁ , Robert D. Pike ₂ , Robert A. Stockland ₁

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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.

中文翻译：

炔烃在金-磷键中的同步插入：立体选择性和可逆原脱氢

已经研究了金磷化合物对炔烃插入金-磷键的敏感性。缺电子炔（DMAD）通过顺式插入金-磷键生成Z-乙烯基金物种，而富电子的内部炔不反应。当 P-手性次膦酸盐用作探针时，发现原脱氢和插入步骤是立体特异性的。与 DMAD 观察到的插入化学相反，缺电子的末端炔烃生成炔基金化合物并通过可逆的原脱氢过程释放二级亚磷酸酯。

更新日期：2021-08-09

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