Rational ligand design in constructing efficient catalyst systems for Suzuki-Miyaura coupling

Rational ligand design in constructing efficient catalyst systems for Suzuki-Miyaura coupling
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DOI:
10.1002/anie.200301753
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发表时间:
2004-04-19
影响因子:
16.6
通讯作者:
Miura, M
Miura, M
中科院分区:
化学1区
文献类型:
--
作者:
Miura, M

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过渡金属催化的交叉偶联反应是目前公认的最有效的碳-碳成键反应之一钯催化芳基卤化物或其合成等价物,如芳基三氟酸酯与芳基金属(M= Mg, Zn, B, Sn, Si等)的偶联通常用于合成联芳基分子,其骨架广泛存在于包括天然产物和有机功能材料在内的重要化合物中(方案1)[1 - 3]。最近,各种体积庞大且富含电子的磷化烷[4,5]和n-杂环碳烯(NHCs)[5],6]作为促进交叉偶联反应的配体。配体可以提供配位不饱和的单膦或单羰基配合物,并加速催化步骤,即氧化加成、金属转化和还原
Transition-metal-catalyzed cross-coupling is now recognized to be one of the most powerful carbon–carbon bondforming reactions.[1] The palladium-catalyzed coupling of aryl halides or their synthetic equivalents, such as aryl triflates, with aryl metals (M= Mg, Zn, B, Sn, Si, etc.) are very often employed in the synthesis of biaryl molecules, whose skeletons are found in a wide range of important compounds including natural products and organic functional materials (Scheme 1).[1–3]Recently, various bulky and electron-rich phosphanes [4, 5] and N-heterocyclic carbenes (NHCs)[5, 6] have been developed as ligands to promote the cross-coupling reaction. The ligands may afford coordinatively unsaturated monophosphane-or monocarbene-ligated complexes and accelerate the catalytic steps, that is, oxidative addition, transmetalation, and reductive