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Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis.
Chemical Reviews ( IF 51.4 ) Pub Date : 2020-06-03 , DOI: 10.1021/acs.chemrev.9b00682 Andrew L Clevenger 1 , Ryan M Stolley 1 , Justis Aderibigbe 1 , Janis Louie 1
Chemical Reviews ( IF 51.4 ) Pub Date : 2020-06-03 , DOI: 10.1021/acs.chemrev.9b00682 Andrew L Clevenger 1 , Ryan M Stolley 1 , Justis Aderibigbe 1 , Janis Louie 1
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A critically important process in catalysis is the formation of an active catalyst from the combination of a metal precursor and a ligand, as the efficacy of this reaction governs the amount of active catalyst. This Review is a comprehensive overview of reactions catalyzed by nickel and an added bidentate phosphine, focusing on the steps transforming the combination of precatalyst and ligand into an active catalyst and the potential effects of this transformation on nickel catalysis. Reactions covered include common cross-coupling reactions, such as Suzuki, Heck, Kumada, and Negishi couplings, addition reactions, cycloadditions, C–H functionalizations, polymerizations, hydrogenations, and reductive couplings, among others. Overall, the most widely used nickel precatalyst with free bidentate phosphines is Ni(cod)2, which accounts for ∼50% of the reports surveyed, distantly followed by Ni(acac)2 and Ni(OAc)2, which account for ∼10% each. By compiling the reports of these reactions, we have calculated statistics of the usage and efficacy of each ligand with Ni(cod)2 and other nickel sources. The most common bidentate phosphines are simple, relatively inexpensive ligands, such as DPPE, DCPE, DPPP, and DPPB, along with others with more complex backbones, such as DPPF and Xantphos. The use of expensive chiral phosphines is more scattered, but the most common ligands include BINAP, Me-Duphos, Josiphos, and related analogs.
中文翻译：
在镍催化中使用双齿膦作为配体的趋势。
催化中一个极其重要的过程是由金属前体和配体的组合形成活性催化剂，因为该反应的功效决定了活性催化剂的量。本综述全面概述了镍和添加的双齿膦催化的反应，重点介绍了将预催化剂和配体的组合转化为活性催化剂的步骤以及这种转化对镍催化的潜在影响。涵盖的反应包括常见的交叉偶联反应，例如 Suzuki、Heck、Kumada 和 Negishi 偶联、加成反应、环加成、C-H 官能化、聚合、氢化和还原偶联等。总体而言，最广泛使用的带有游离双齿膦的镍预催化剂是 Ni(cod) 2，占调查报告的~50%，其次是Ni(acac) 2和Ni(OAc) 2，分别占~10%。通过汇编这些反应的报告，我们计算了每种配体与 Ni(cod) 2和其他镍源的使用和功效的统计数据。最常见的二齿膦是简单、相对便宜的配体，例如 DPPE、DCPE、DPPP 和 DPPB，以及其他具有更复杂骨架的配体，例如 DPPF 和 Xantphos。昂贵的手性膦的使用较为分散，但最常见的配体包括BINAP、Me-Duphos、Josiphos及相关类似物。
更新日期：2020-07-08
中文翻译：
在镍催化中使用双齿膦作为配体的趋势。
催化中一个极其重要的过程是由金属前体和配体的组合形成活性催化剂，因为该反应的功效决定了活性催化剂的量。本综述全面概述了镍和添加的双齿膦催化的反应，重点介绍了将预催化剂和配体的组合转化为活性催化剂的步骤以及这种转化对镍催化的潜在影响。涵盖的反应包括常见的交叉偶联反应，例如 Suzuki、Heck、Kumada 和 Negishi 偶联、加成反应、环加成、C-H 官能化、聚合、氢化和还原偶联等。总体而言，最广泛使用的带有游离双齿膦的镍预催化剂是 Ni(cod) 2，占调查报告的~50%，其次是Ni(acac) 2和Ni(OAc) 2，分别占~10%。通过汇编这些反应的报告，我们计算了每种配体与 Ni(cod) 2和其他镍源的使用和功效的统计数据。最常见的二齿膦是简单、相对便宜的配体，例如 DPPE、DCPE、DPPP 和 DPPB，以及其他具有更复杂骨架的配体，例如 DPPF 和 Xantphos。昂贵的手性膦的使用较为分散，但最常见的配体包括BINAP、Me-Duphos、Josiphos及相关类似物。
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