Preparation of Tertiary Phosphines Using a Convenient Form of Lithium Diphenylphosphide

Clark, Peter W.

doi:10.1080/00304947909458131

Cited by 19 publications

(1 citation statement)

References 9 publications

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“…In the initial experiments, complex 95 reacted with a solution of LiPPh 2 in THF purchased from Sigma-Aldrich. Reactions of the dimeric cyclopalladated complex 95 in THF with LiPPh 2 synthe- sized in our lab from either PPh 3 [72][73][74], or ClPPh 2 [75][76][77] or HPPh 2 [78,79] led to the formation of either μ-Cl-μ-PPh 2 complex 97 using 1 equiv. No traces of the desired aminophosphine 90 were formed.…”

Section: Reactions Of Cyclopalladated Complexes With Metal Phosphidesmentioning

confidence: 97%

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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Section: Reactions Of Cyclopalladated Complexes With Metal Phosphidesmentioning

confidence: 97%

Synthesis of Aminophosphines and Their Applications in Catalysis

Stepanova¹,

Smoliakova²

2012

COC

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Polydentate Phosphines: Their Syntheses, Structural Aspects, and Selected Applications

Cotton

Hong

1992

Progress in Inorganic Chemistry

103

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Synthesis and Structure of a Cyclic Complex of Digold Sulfide Au₂S and of Related Compounds

1995

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1,4‐Bis(diphenylphosphanylmethyl)benzene (1) was converted into its bis[chlorogold(I)] complex [1 · (AuCl)2] upon treatment with two equivalents of chloro(dimethyl sulfide)‐gold(I). The reaction of 1 · (AuCl)2 with one equivalent of silver tetrafluoroborate afforded a cyclic di[gold(I)]chloronium tetrafluoroborate [1 · Au2Cl+ BF‐4]. Substitution of chloride in 1 · (AuCl)2 by sodium methanethiolate in wet chloroform, gave the bis[methylthiogold(I)] complex 1 · (AuSMe)2], while with sodium sulfide a cyclic complex 1 · Au2S was obtained. Reaction of 1 · (AuCl)2 with two equivalents of AgBF4 followed by treatment with diphenyldisulfide or sodium methanethiolate yielded the cyclic methyl/phenylsulfonium tetrafluoroborates 1 · Au2SPh+ BF‐4 and 1 · Au2SMe+BF‐4, respectively. All compounds were identified on the basis of their analytical and spectroscopic data. The crystal structures of 1 · (AuCl)2, 1 · (AuSMe)2, and 1 · Au2S have been determined. The Au2S complex has a cyclic structure with a narrow Au‐S‐Au angle of 86.7(1)° indicating a significant intraannular Au…Au interaction.

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Preparation of Tertiary Phosphines Using a Convenient Form of Lithium Diphenylphosphide

Cited by 19 publications

References 9 publications

Synthesis of Aminophosphines and Their Applications in Catalysis

Synthesis of Aminophosphines and Their Applications in Catalysis

Polydentate Phosphines: Their Syntheses, Structural Aspects, and Selected Applications

Synthesis and Structure of a Cyclic Complex of Digold Sulfide Au₂S and of Related Compounds

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Preparation of Tertiary Phosphines Using a Convenient Form of Lithium Diphenylphosphide

Cited by 19 publications

References 9 publications

Synthesis of Aminophosphines and Their Applications in Catalysis

Synthesis of Aminophosphines and Their Applications in Catalysis

Polydentate Phosphines: Their Syntheses, Structural Aspects, and Selected Applications

Synthesis and Structure of a Cyclic Complex of Digold Sulfide Au2S and of Related Compounds

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Synthesis and Structure of a Cyclic Complex of Digold Sulfide Au₂S and of Related Compounds