Biaryl monophosphine ligands in palladium-catalyzed C-N coupling: An updated User's guide

Biaryl monophosphine ligands in palladium-catalyzed C-N coupling: An updated User's guide
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DOI:
10.1016/j.tet.2019.05.003
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发表时间:
2019-08-09
期刊:
影响因子:
2.1
通讯作者:
Buchwald, Stephen L.
Buchwald, Stephen L.
中科院分区:
化学3区
文献类型:
--
作者:
Ingoglia, Bryan T.;Wagen, Corin C.;Buchwald, Stephen L.

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在过去的三十年里,钯催化的交叉偶联反应已经成为有机合成的支柱。特别地,衍生自联芳基单膦的催化剂在温和的反应条件下形成C-N键中显示出广泛的实用性。本文总结了以联芳基单膦为支持配体的各种C-N交叉偶联反应,旨在指导合成化学家寻找最适合特定偶联反应的配体和条件。序言:当我得知我与John F.当我看到加州大学伯克利分校的哈特维希时,我感到一种巨大的成就感。这并不是我个人的成就,而是我的研究小组(以及约翰的研究小组)在开发新化学方面的成就,这种化学既有趣又实用。后一个方面是我们选择写这篇综述的原因,以帮助该领域的从业者在自己的研究工作中更广泛,有效和预测地利用钯催化的C-N偶联反应。我们注意到,虽然我们将这篇综述限制在使用联芳基膦配体的反应中,但存在许多其他良好的替代品。(C)2019由Elsevier Ltd.出版
Over the past three decades, Pd-catalyzed cross-coupling reactions have become a mainstay of organic synthesis. In particular, catalysts derived from biaryl monophosphines have shown wide utility in forming C-N bonds under mild reaction conditions. This work summarizes a variety of C-N cross-coupling reactions using biaryl monophosphines as supporting ligands, with the goal of directing synthetic chemists towards the ligands and conditions best suited for a particular coupling.Prelude: When I learned that I had received the 2018 Tetrahedron Prize for Creativity in Organic Chemistry, jointly with Professor John F. Hartwig of UC Berkeley, I felt a sense of great accomplishment. Accomplishment not specifically for me, but by my research group (and that of John's) in developing new chemistry that was both intrinsically interesting and of practical utility. The latter aspect is the reason that we have chosen to write this review to help practitioners in the field utilize palladium-catalyzed C-N coupling reactions more broadly, efficiently, and predictively in their own research efforts. We note that while we have limited this review to reactions using biaryl phosphine ligands, that many other good alternatives exist. (C) 2019 Published by Elsevier Ltd.