Asymmetric Synthesis of Functionalized 1,3-Diphosphines via Chiral Palladium Complex Promoted Hydrophosphination of Activated Olefins

Yuan, Mingjun; Zhang, Na; Pullarkat, Sumod A.; Li, Yongxin; Liu, Fengli; Pham, Phuong-Tu; Leung, Pak‐Hing

doi:10.1021/ic9018053

Cited by 28 publications

(9 citation statements)

References 51 publications

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“…In the proposed mechanism the catalyst 55 acts as a base toward the diarylphosphine 25c . Some other examples of palladium-catalyzed asymmetric hydrophosphination are the addition of diphenylphosphine to α,β-unsaturated ketones [127–128], esters [129], sulfonic esters [130] or to dienones [131]. The proposed mechanism is ubiquitous in metal-catalyzed hydrophosphination involving a P–H oxidative addition, insertion of the olefin into the Pd–H bond and reductive elimination.…”

Section: Reviewmentioning

confidence: 99%

Preparation of phosphines through C–P bond formation

Wauters¹,

Debrouwer²,

Stevens³

2014

Beilstein J. Org. Chem.

175

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Section: Reviewmentioning

confidence: 99%

Preparation of phosphines through C–P bond formation

Wauters¹,

Debrouwer²,

Stevens³

2014

Beilstein J. Org. Chem.

175

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“…The best results were observed in the reaction of HPPh 2 with the simple symmetric enone 70a (entry 1). phosphines [53,54] and diphosphines [55][56][57][58]. The Leung group has reported a number of significant studies on the use of enantiopure cyclopalladated complexes as templates (auxiliaries) for asymmetric synthesis of compounds possessing ligand properties, e.g.…”

Section: Hydrophosphination Of -Unsaturated Carboxylic Acids Aldehmentioning

confidence: 99%

Synthesis of Aminophosphines and Their Applications in Catalysis

Stepanova¹,

Smoliakova²

2012

COC

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The review describes preparation of P,N-bidentate ligands without a P-N bond and their use in asymmetric catalysis. Diverse types of aminophosphines are considered with emphasis on P,N-ferrocene ligands, phosphino-oxazolines and phosphinopyridines. The following major synthetic approaches to aminophosphines and related compounds are summarized: (i) via lithiation, (ii) the use of Grignard reagents, (iii) nucleophilic substitution using metal phosphides, (iv) Staudinger method, (v) hydrophosphination of , -unsaturated carbonyl compounds, (vi) Cu-and Pd-catalyzed C-P bond formation reactions, and (vii) reactions of cyclopalladated complexes with metal phosphides and HPPh2. Highlights of aminophosphine applications in asymmetric synthesis include their use in hydrogenation, hydrosilylation, and hydroboration reactions as well as in various transformations leading to a C-C bond formation such as Suzuki coupling, Meerwein-Eschenmoser-Claisen rearrangement, Mukaiyama aldol reaction, Tsuji allylation and ethylene oligomerization.ligands in a number of metal-catalyzed transformations are presented. Synthesis and applications of aminophosphines with a P-N bond are not included in this review. Preparation of -aminophosphoryl compounds [22] as well as reactions leading to the C-P bond formation using diphenylphosphine oxide HP(O)Ph 2 and dialkyl phosphites (RO) 2 P(O)H (see, for example, recent reports of Keglevich [23,24]) are also outside of the scope of this review. MAJOR CLASSES OF AMINOPHOSPHINES WITHOUT A P-N BONDThe majority of reported P,N-ligands without a P-N bond can be divided into several major categories (Chart 1). The first group is based on the ligands derived from ferrocene. Representatives of this group have been the first examples of chiral P,N-ligands successfully applied in asymmetric catalysis [25]. The second major group includes phosphino-oxazolines (PHOX), which are among the most successful catalysts in metal-catalyzed asymmetric reactions [6,7,[26][27][28][29][30][31][32]. The third group consists of chiral aliphatic P,Nligands, which can be obtained by a modification of a naturally available chiral source, e.g. amino acids [33,34]. The fourth group is formed by structurally diverse binaphthyl derivatives, so-called MAP ligands, which combine axial chirality with soft and hard coordination properties of phosphorus and nitrogen atoms [35]. The next group worth mentioning is represented by P,N-ligands with the pyridine or quinoline framework, e.g. QUINAP [8,36]. Representatives of the last type of aminophosphines have either phosphorusor nitrogen-containing non-aromatic heterocycle [37,38]. Separately from these major groups stand the ligands with structural features from two or more of the aforementioned ligand types, e.g. oxazoline-ferrocene [39] or pyrrolidine-MAP-derivatives [10]. SYNTHETIC APPROACHES TO AMINOPHOSPHINESDevelopment of synthetic routes to aminophosphines without a P-N bond recently received a lot of attention due to a growing number of impressive applications of these ligands in a...

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“…We had previously reported that orthometalated [1-(dimethylamino)ethyl]naphthalene palladium(II) complexes and platinum(II) complexes can act as a chiral template that promotes various reactions, namely, [4+2] cycloaddition, − hydrophosphination, − hydroamination, − and hydroarsination reactions. , These reactions can generate many useful P -stereogenic phosphines under mild reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Metal Effects on the Asymmetric Cycloaddition Reaction between 3,4-Dimethyl-1-phenylphosphole and Sulfoxide

Zhang

et al. 2015

Organometallics

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The orthometalated [1-(dimethylamino)ethyl]naphthalene platinum(II) complex has been used successfully to promote the asymmetric cycloaddition reaction between 3,4-dimethyl-1-phenylphosphole and sulfoxide in high selectivity. The exo-cycloadduct coordinated to the platinum template as bidentate chelates via their phosphorus and sulfur atoms. The dichloro platinum complexes could be crystallized and were stable in the solid state as well as in solution. Optically pure P−S bidentate ligands could be liberated from these dichloro complexes by treatment with aqueous potassium cyanide. The study also highlights the difference in reactivity and mode of substrate activation between an earlier study involving a Pd analogue of the template and the current results.

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Asymmetric Synthesis of Functionalized 1,3-Diphosphines via Chiral Palladium Complex Promoted Hydrophosphination of Activated Olefins

Cited by 28 publications

References 51 publications

Preparation of phosphines through C–P bond formation

Preparation of phosphines through C–P bond formation

Synthesis of Aminophosphines and Their Applications in Catalysis

Metal Effects on the Asymmetric Cycloaddition Reaction between 3,4-Dimethyl-1-phenylphosphole and Sulfoxide

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