Category: 1608-26-0

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Oxidative addition and reductive elimination are key steps in a wide variety of catalytic reactions mediated by transition-metal complexes. Historically, this reactivity has been considered to be the exclusive domain of d-block elements. However, this paradigm has changed in recent years with the demonstration of transition-metal-like reactivity by main-group compounds. This Review highlights the substantial progress achieved in the past decade for the activation of robust single bonds by main-group compounds and the more recently realized activation of multiple bonds by these elements. We also discuss the significant discovery of reversible activation of single bonds and distinct examples of reductive elimination at main-group element centers. The review consists of three major parts, starting with oxidative addition of single bonds, proceeding to cleavage of multiple bonds, and culminated by the discussion of reversible bond activation and reductive elimination. Within each subsection, the discussion is arranged according to the type of bond being cleaved or formed and considers elements from the left to the right of each period and down each group of the periodic table. The majority of results discussed in this Review come from the past decade; however, earlier reports are also included to ensure completeness.

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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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The synthesis and characterization of a series of novel chiral P,O ferrocenyl ligands obtained from the reaction of racemic (9) or enantiomerically pure ((R)-9 or (S)-9) 2-thiodiphenylphosphino(hydroxymethyl)ferrocene with alcohols is described. The use of para-methylbenzylalcohol, ethanol and (1R,2S,5R)-menthol gives rise to three ligands (10, 11 and 12 respectively) possessing planar chirality. All compounds have been characterized by multinuclear NMR and mass spectrometry. Compounds 12 and 12a (the protected form of phosphine 12 with a PS bond) present both planar and central chirality giving rise to two diastereoisomers differing in configuration (R or S) of the ferrocenyl fragment. Compound (S)-12a has been characterized by single-crystal X-ray diffraction. Kinetic studies realized at three different temperatures (40, 50 and 60 C) show good yields in the asymmetric Suzuki-Miyaura synthesis of substituted binaphthalenes using 1-naphthalenboronic acid and 1-bromo-2-methylnaphthalene. The best enantioselectivity (37% ee) was obtained with ligand (R)-12.

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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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, molecular formula is P[N(CH3)2]3. In a Article，once mentioned of 1608-26-0, Application In Synthesis of Tris(dimethylamino)phosphine

A family of new chiral phosphoramidite ligands based on 3,3?-disubstituted (S)-BINOL have been successfully synthesized. The chiral phosphoramidite ligands were subsequently applied to the copper(II)-catalyzed enantioselective addition of diethylzinc to beta-substituted enones, giving the desired chiral adducts with enantioselectivities of up to 93% ee and high yields (up to 88%).

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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

In an article, published in an article, once mentioned the application of 1608-26-0, Name is Tris(dimethylamino)phosphine
,molecular formula is P[N(CH3)2]3, is a conventional compound. this article was the specific content is as follows.category: chiral-phosphine-ligands

The highly functional chromio nitrile ylides Cr(CO)5C=N-C(Cl)- PR3 (R = Ph, NMe2) (2a, b) form readily in mixtures of Cr(CO)5CNCCl3 (1) with the respective phosphanes. Their reactions without isolation with the acylating agent Cr(CO)5CN(C=O)Ar (Ar = C6H4-P-NO2), MeO2CC? CCO2Me, ketones (R2C=O, R = Me, Et; 2R = 9-fluorenediyl) and phenyl isocyanate to give the Cl/COAr-substitution- (6a), alkyne insertion- (10) and [3+2] cycloaddition products (13, 14) are described. Formation of the latter is accompanied by an interligand CC coupling with loss of P(NMe 2)3 and OP(NMe2)3 (after hydrolysis). Their reactions are compared with, those of the parent compounds LnMCN-C(H)-PPh3.

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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

1608-26-0, Name is Tris(dimethylamino)phosphine
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High filling fraction gallium phosphide (GaP) inverse opals were fabricated by atomic layer deposition within the void spaces of silica colloidal crystal templates. Depositions were performed from 400 to 500 C using trimethylgallium and tris(dimethylamino)phosphine precursors. The resulting films were characterized by optical reflectance, which indicated infiltration as high as 100% of the conformal film growth maximum, corresponding to a volume filling fraction of 0.224. X-ray diffraction measurements confirmed the crystallinity of the film. These results indicate the fabrication of three-dimensional photonic crystals using a III-V optoelectronic material with sufficient dielectric contrast to form a full photonic band gap in the visible.

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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.1608-26-0, Name is Tris(dimethylamino)phosphine
, molecular formula is P[N(CH3)2]3. In a Article，once mentioned of 1608-26-0, Recommanded Product: 1608-26-0

Diumycinol <2(Z),6(E)-12-(2-methylene-6,6-dimethyl-1-cyclohexyl)-11-methylene-3,8,8-trimethyldodeca-2,6-dien-1-ol>, a hydrolytic product of the antibiotic diumycin, was assembled from three fragments: 1-(2-phenylsulphonylethyl)-2-methylene-6,6-dimethylcyclohexane (28), 3-(2-iodoethyl)-3-methyloxetane (39), and (Z)-1-benzyloxy-6-phenylsulphonyl-3-methylhex-2-ene (3).An efficient synthesis of 2-methylene-6,6-dimethylcyclohexylmethanol (15) (gamma-cyclogeraniol) was accomplished by a <2,3>sigmatropic rearrangement of 3,3-dimethylcyclohex-1-enylmethoxymethyl-lithium (17).

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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.1608-26-0, Name is Tris(dimethylamino)phosphine
, molecular formula is P[N(CH3)2]3. In a Article，once mentioned of 1608-26-0, HPLC of Formula: P[N(CH3)2]3

Eleven chiral trivalent or quatrivalent phosphorus reagents were synthesized starting from L-proline, D-camphor, (+)- or (-)-1,1′-binaphthalene-2,2′-diol, (-)-alpha-phenylethylamine, etc. and their application as catalysts in asymmetric borane reduction of N-phenyl imine of acetophenone was preliminary investigated. N-Phenyl alpha-phenylethylamine was obtained in good yield with low to moderate enantioselectivity.

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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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The structural isomerism in R3PSe(Ph)I compounds and the ionic structure of [(Me2N)3PSePh]I were discussed. The ionic compound [(Me2N)3PSePh]I was found to contain a long Se-I contact, 3.825 A, and a bent P-Se-I angle, 114.5 A. The analysis showed discrepancy in the N-P-N angles, two being similar, 105.1 A and 107.0 A with the third was significantly greater.

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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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A racemic 1,1?-spirobitetralin-8,8?-diol (SBITOL) was conveniently synthesized from 3-methoxybenzaldehyde in 26 % yield over 9 steps and resolved via its bis-(S)-camphorsulfonates. The corresponding chiral spirobitetraline monophosphoramidite ligands have been prepared and their rhodium complexes were applied in the asymmetric hydrogenation of dehydroamino esters with good to excellent enantioselectivities (up to 99.3% ee).

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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

In an article, published in an article, once mentioned the application of 1608-26-0, Name is Tris(dimethylamino)phosphine
,molecular formula is P[N(CH3)2]3, is a conventional compound. this article was the specific content is as follows.Computed Properties of P[N(CH3)2]3

Natural abundance 13C NMR studies have been carried out on a series of organophosphorus compounds possessing P-N bonds.For the first time a one-bond temperature-dependent 13C-31P nuclear spin coupling was observed for the P-phenyl carbons in bis(N,N-dibenzylamino)phenylphosphine (0-9 Hz) and bis(N,N-diethylamino)phenylphosphine (0-2 Hz).This temperature-dependent behavior can be rationalized in terms of free rotation about the phenyl phosphorus bond with concomitant hindered rotation about the P-N bonds.A conformational preference for the nitrogen and phosphorus lone pairs to exist in the trans orientation is indicated.In the similarly substituted 5-membered heterocyclic ring compound, 1,3-dimethyl-2-phenyl-1,3-diazaphospholidine, the phenyl one-bond coupling increases to (-) 42.1 Hz and becomes temperature independent.These data suggest that 1J(PC) is very responsive to electronic effects.

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Reference：
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate