Quaternary and Tertiary Carbon Centers Synthesized via Gallium-Catalyzed Direct Substitution of Unfunctionalized Propargylic Alcohols with Boronic Acids
Quaternary and Tertiary Carbon Centers Synthesized via Gallium-Catalyzed Direct Substitution of Unfunctionalized Propargylic Alcohols with Boronic Acids
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DOI：
10.1021/acs.orglett.2c02612
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发表时间：
2022-09-13
期刊：
影响因子：
5.2
通讯作者：
May, Jeremy A.
中科院分区：
文献类型：
--
作者：
Donald, Clayton P.;Boylan, Amy;May, Jeremy A.
(IPr)GaCl3/AgSbF6、AgSbF6和GaCl3催化仲丙醇和叔丙醇的羟基通过C-C键被有机硼酸取代，GaCl3有效地合成了全碳季丙二醇中心。这些催化剂在带有烷基取代基的碳上进行取代，这对于其他系统来说是个问题。由此产生了高度受阻的碳立构中心，包括带有双邻位取代的芳环的四元中心，这是用传统方法难以获得的。
(IPr)GaCl3/AgSbF6, AgSbF6, and GaCl3 catalyzed substitution of the hydroxyl of secondary and tertiary propargylic alcohols with organoboronic acids via C-C bond formation, and GaCl3 effectively synthesized all-carbon quaternary propargylic centers. These catalysts performed the substitution at carbons bearing alkyl substituents, which has been problematic for other systems. Highly hindered carbon stereocenters were thus produced, including quaternary centers bearing doubly ortho-substituted aryl rings, that are difficult to access with traditional methods.