钯催化烯丙基卤化锌与芳基和乙烯基亲电试剂的完全线性选择性根岸交叉偶联反应。
Palladium-catalyzed completely linear-selective Negishi cross-coupling of allylzinc halides with aryl and vinyl electrophiles.
作者信息
Yang Yang, Mustard Thomas J L, Cheong Paul Ha-Yeon, Buchwald Stephen L
机构信息
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139 (USA).
出版信息
Angew Chem Int Ed Engl. 2013 Dec 23;52(52):14098-102. doi: 10.1002/anie.201308585. Epub 2013 Nov 8.
Abstract
a general and practical palladium-catalyzed linear-selective Negishi coupling of 3,3-disubstituted allylzinc reagents with aryl, heteroaryl and vinyl electrophiles at ambient temperature is described. This method provides an effective means to access a wide range of prenylated arenes or skipped dienes in a completely linear-selective fashion, as demonstrated by a concise synthesis of the anti-HIV natural product siamenol. Finally, DFT calculations shed light on the origin of the excellent regioselectivity observed with the current catalyst system.
摘要
本文描述了一种通用且实用的钯催化的3,3-二取代烯丙基锌试剂与芳基、杂芳基和乙烯基亲电试剂在室温下的线性选择性根岸偶联反应。该方法提供了一种有效的手段，能够以完全线性选择性的方式获得多种异戊烯基化芳烃或跳跃式二烯，抗艾滋病毒天然产物暹罗醇的简洁合成即证明了这一点。最后，密度泛函理论计算揭示了当前催化剂体系所观察到的优异区域选择性的来源。
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