Asymmetric Synthesis of P-Stereogenic Secondary Phosphine-Boranes by an Unsymmetric Bisphosphine Pincer-Nickel Complex

Wang, Chuanyong; Huang, Kesheng; Ye, Jie; Weng, Duan

doi:10.1021/jacs.1c02772

Cited by 118 publications

(42 citation statements)

References 60 publications

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“…A chiral pincer bisphosphane Ni complex was used in the first highly enantioselective catalytic synthesis of P-stereogenic secondary phosphane-boranes by the asymmetric hydrophosphination of electron-deficient alkenes with phenylphosphane. Various P-stereogenic secondary phosphane-boranes were obtained in 57-92% yields with up to 99% ee [54]. The Togni group developed the asymmetric hydrophosphination of vinyl nitriles catalyzed by a dicationic Ni-based complex yielding the desired phosphane product with 32-94% ee [55,56] (Figure 14).…”

Section: Hydrophosphination Reactions Of Alkenes and Alkynesmentioning

confidence: 99%

Nickel Complexes in C‒P Bond Formation

et al. 2021

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This review is a comprehensive account of reactions with the participation of nickel complexes that result in the formation of carbon–phosphorus (C‒P) bonds. The catalytic and non-catalytic reactions with the participation of nickel complexes as the catalysts and the reagents are described. The various classes of starting compounds and the products formed are discussed individually. The several putative mechanisms of the nickel catalysed reactions are also included, thereby providing insights into both the synthetic and the mechanistic aspects of this phosphorus chemistry.

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Section: Hydrophosphination Reactions Of Alkenes and Alkynesmentioning

confidence: 99%

Nickel Complexes in C‒P Bond Formation

et al. 2021

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“…Very recently, Wang et al demonstrated the synthesis of unsymmetrical PCP′ pincer nickel complexes bearing a phosphine-phosphinite ligand with a stereogenic carbon center [ 152 ]. The corresponding enantiopure nickel complexes 55a and 55b were obtained via a convenient one-pot three-step reaction ( Scheme 31 ).…”

Section: Other Types Of Complexesmentioning

confidence: 99%

Recent Advances in Chemistry of Unsymmetrical Phosphorus-Based Pincer Nickel Complexes: From Design to Catalytic Applications

et al. 2021

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Pincer complexes play an important role in organometallic chemistry; in particular, their use as homogeneous catalysts for organic transformations has increased dramatically in recent years. The high catalytic activity of such bis-cyclometallic complexes is associated with the easy tunability of their properties. Moreover, the phosphorus-based unsymmetrical pincers showed higher catalytic activity than the corresponding symmetrical analogues in several catalytic reactions. However, in modern literature, an increasing interest in the development of catalysts based on non-precious metals is observed. For example, nickel, which is an affordable and sustainable analogue of platinum and palladium, known for its low toxicity, has attracted increasing attention in the catalytic chemistry of transition metals in recent years. Thus, this mini-review is devoted to the recent advances in the chemistry of unsymmetrical phosphorus-based pincer nickel complexes, including the ligand design, the synthesis of nickel complexes and their catalytic applications.

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“…A wide range of phosphine chemistry has been developed, with metal catalyzed hydrophosphination being one of the most economic avenues for P-C bond formation. Though significant progress has occurred [1,7,[15][16][17][18][19][20][21][22][23][24], challenges remain for this transformation, with catalyst and substrate scope being two key avenues for improvement [1,15,[25][26][27][28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Effect of Photolysis on Zirconium Amino Phenoxides for the Hydrophosphination of Alkenes: Improving Catalysis

Novas

Morris

Liptak

et al. 2021

Preprint

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A comparative study of amino phenoxide zirconium catalysts in the hydrophosphination of alkenes with diphenylphosphine reveals enhanced activity upon irradiation. The origin of improved reactivity is hypothesized to result from substrate insertion upon an n to d charge transfer of a Zr–P bond in the excited state of putative phosphido (Zr–PR2) intermediates. TD-DFT analysis reveals the lowest lying excited state in the proposed active catalysts are dominated by a P 3p to Zr 4d MLCT, presumably leading to enhanced catalysis. This hypothesis follows from triamidoamine-supported zirconium catalysts but demonstrates the generality of photocatalytic hydrophosphination with d0 metals.

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Asymmetric Synthesis of P-Stereogenic Secondary Phosphine-Boranes by an Unsymmetric Bisphosphine Pincer-Nickel Complex

Cited by 118 publications

References 60 publications

Nickel Complexes in C‒P Bond Formation

Nickel Complexes in C‒P Bond Formation

Recent Advances in Chemistry of Unsymmetrical Phosphorus-Based Pincer Nickel Complexes: From Design to Catalytic Applications

Effect of Photolysis on Zirconium Amino Phenoxides for the Hydrophosphination of Alkenes: Improving Catalysis

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