Gold Catalysis: Isolation of Vinylgold Complexes Derived from Alkynes
Gold Catalysis: Isolation of Vinylgold Complexes Derived from Alkynes
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DOI：
10.1002/anie.200903134
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发表时间：
2009-01-01
影响因子：
16.6
通讯作者：
Rominger, Frank
中科院分区：
文献类型：
--
作者：
Hashmi, A. Stephen K.;Schuster, Andreas M.;Rominger, Frank
金催化的有机转化仍然是有机化学中发展最快的领域之一最重要的反应模式是将亲核试剂添加到CÀC多个键上（主要是炔烃而不是烯或烯烃）。在2000年，我们证明了烯基酮的羰基氧原子可以作为亲核试剂，并通过5-内三角环化形成呋喃在2004年，我们报道了n -丙基氨基甲酸酯的5-外环化，[3]和2007年我们报道了n -炔基氨基甲酸酯的5-内环化。这前两篇论文开创了一整套金催化环化反应的发展，包括羰基作为亲核试剂来传递不同类型的杂环。[5-7]本文报道了具有内炔基的n -丙基羧酰胺环化的新发现。
Gold-catalyzed organic transformations still represent one of the fast growing areas of organic chemistry.[1] The most important reactivity pattern is the addition of nucleophiles to CÀC multiple bonds (mostly alkynes rather than allenes or alkenes). In 2000, we demonstrated that carbonyl oxygen atoms of allenyl ketones can serve as nucleophiles, and form furans by a 5-endo-trig cyclization.[2] In 2004, we reported the use of N-propargyl carboxamides 1, having terminal alkynyl groups (Scheme 1, R2= H), for 5-exo-dig cyclizations,[3] and in 2007 we reported the 5-endo-dig cyclization of N-alkynyl carbamates.[4]These first two papers have initiated the development of an entire family of gold-catalyzed cyclizations involving carbonyl groups as nucleophiles to deliver different types of heterocycles.[5–7] Herein we report new findings on the cyclization of N-propargyl carboxamides having internal alkynyl groups.