A highly active catalyst for Pd-catalyzed amination reactions: cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides.

A highly active catalyst for Pd-catalyzed amination reactions: cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides.
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DOI:
10.1021/ja8055358
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发表时间:
2008-10-15
影响因子:
15
通讯作者:
Buchwald, Stephen L.
Buchwald, Stephen L.
中科院分区:
化学1区
文献类型:
--
作者:
Fors, Brett P.;Watson, Donald A.;Biscoe, Mark R.;Buchwald, Stephen L.

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报道了一种基于新型联芳基单膦配体(BrettPhos)的催化剂体系,该体系对C-N交叉偶联反应表现出优异的反应活性。该催化剂体系使得能够使用甲磺酸芳基酯作为C-N键形成反应中的偶联配偶体。此外,BrettPhos的使用允许在低催化剂负载和快速反应时间下高度选择性地单芳基化一系列伯脂族胺和苯胺,包括甲胺的第一单芳基化。最后,包括BrettPhos的氧化加成络合物,这提供了深入了解该系统的反应性的起源。
A catalyst system based on a new biarylmonophosphine ligand (BrettPhos) that shows excellent reactivity for C–N cross-coupling reactions is reported. This catalyst system enables the use of aryl mesylates as a coupling partner in C–N bond-forming reactions. Additionally, the use of BrettPhos permits the highly selective monoarylation of an array of primary aliphatic amines and anilines at low catalyst loadings and with fast reaction times, including the first monoarylation of methylamine. Lastly, oxidative addition complexes of BrettPhos are included, which provide insight into the origin of reactivity for this system.
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