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Usage

Uses

Used in Organic and Inorganic Chemistry:
(1R,2R)-BIS[(2-METHOXYPHENYL)PHENYLPHOSPHINO]ETHANE DIBORANE is used as a ligand in various organic and inorganic chemistry applications, particularly in the field of catalysis. The presence of the phosphine groups in the compound allows for coordination with transition metals, making it useful in various catalytic reactions.
Used in Catalysis:
(1R,2R)-BIS[(2-METHOXYPHENYL)PHENYLPHOSPHINO]ETHANE DIBORANE is used as a ligand in catalysis for its ability to coordinate with transition metals. This coordination enhances the reactivity and selectivity of the catalytic reactions, making it a valuable component in the development of new catalysts.
Used in Chemical Synthesis:
(1R,2R)-BIS[(2-METHOXYPHENYL)PHENYLPHOSPHINO]ETHANE DIBORANE is used in chemical synthesis due to the unique reactivity of the boron atoms in the compound. This reactivity allows for the formation of new chemical bonds and the synthesis of complex molecules, making it a versatile compound in the field of chemical synthesis.

Upstream product

• 1316041-04-9 (R_P,R_P)-1,2-bis[(o-hydroxyphenyl)(phenyl)phosphino-P-borane]ethane 
• 1316041-04-9 C₂₆H₃₀B₂O₂P₂ 
• 74-88-4 methyl iodide 
• 127687-02-9 (S)-o-anisyl(2-iodoethyl)phenylphosphine-borane 
• 97764-41-5 (S)-(+)-(o-anisyl)(methyl)phenylphosphine/borane complex 
• 14044-65-6 borane-THF 
• 55739-59-8 (1R,1R')-(-)-1,1'-(1,2-ethanediyl)bis[1-(2-methoxyphenyl)-1-phenyl]phosphine oxide 
• 578-57-4 2-bromoanisole 
• 19315-13-0 methyl(phenyl)phosphineoxide 
• 35143-99-8 (R_p)-(2-methoxyphenyl)methylphenylphosphine oxide 
• 1155850-63-7 (R_P,R_P)-1,2-bis[(methoxy)(phenyl)phosphino-P-borane]ethane 

Downstream Products

• 55739-58-7 (R_P,R_P)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane 
• 55739-58-7 (S(P),S(P))-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane 
• 917029-49-3 (R_P,R_P)-1,2-bis[(phenyl)(2-triisopropylsiloxyphenyl)phosphino-P-borane]ethane 
• 1316041-11-8 (R_P,R_P)-1,2-bis{[2-(N-tert-butylcarbamoylmethoxy)phenyl](phenyl)phosphino-P-borane}ethane 
• 917029-53-9 (R_P,R_P)-1,2-bis{[2-(tert-butoxycarbonylmethoxy)phenyl](phenyl)phosphino-P-borane}ethane 
• 917029-52-8 (R_P,R_P)-1,2-bis{[2-(9-anthrylmethoxy)phenyl](phenyl)phosphino-P-borane}ethane 
• 81964-01-4 (R_P,R_P)-1,2-bis[(o-hydroxyphenyl)(phenyl)phosphino]ethane 
• 1316041-35-6 (R_P,R_P)-1,2-bis[(2-(diphenylphosphinyloxy)phenyl)(phenyl)phosphino]ethane 
• 1316041-34-5 (R_P,R_P)-1,2-bis{(phenyl)[2-(p-tosyloxy)phenyl]phosphino}ethane 
• 1316041-31-2 (R_P,R_P)-1,2-bis[(2-benzoyloxyphenyl)(phenyl)phosphino]ethane 
• 917029-70-0 (R_P,R_P)-1,2-bis[(phenyl)(2-pivaloyloxyphenyl)phosphino]ethane 
• 81964-02-5 (R_P,R_P)-1,2-bis[(2-acetoxyphenyl)(phenyl)phosphino]ethane 
• 917029-71-1 (R_P,R_P)-1,2-bis[(phenyl)(2-triisopropylsiloxyphenyl)phosphino]ethane 
• 1316041-28-7 (R_P,R_P)-1,2-bis{[2-(N-tert-butylcarbamoylmethoxy)phenyl](phenyl)phosphino}ethane 

Relevant academic research and scientific papers

P-Chiral Phosphines Enabled by Palladium/Xiao-Phos-Catalyzed Asymmetric P-C Cross-Coupling of Secondary Phosphine Oxides and Aryl Bromides

The development of transition-metal-catalyzed methods for the synthesis of P-chiral phosphine derivatives poses a considerable challenge. Herein, we present a direct Pd/Xiao-Phos-catalyzed cross-coupling reaction of easily accessible secondary phosphine o

Profiling the tuneable R-SMS-Phos structure in the rhodium(i)-catalyzed hydrogenation of olefins: The last stand?

A diversified family of enantiopure P-stereogenic "R-SMS-Phos" {R-SMS-Phos = 1,2-bis[(o-RO-phenyl)(phenyl)phosphino]ethane} ligands wherein R = branched or heteroatom-substituted alkyl, aralkyl, silyl, acyl, sulfonyl, etc. was screened for the Rh(i)-catalyzed hydrogenation of a representative set of olefinic substrates. This systematic and detailed investigation revealed a marked beneficial impact on enantioselectivity and catalyst activity in comparison to Knowles' ultimate DiPAMP {DiPAMP = 1,2-bis[(o-anisyl)(phenyl) phosphino]ethane} design. Mutant ligands with highly enhanced properties possessing particular features wherein the DiPAMP structure is found embedded were identified. The Royal Society of Chemistry 2011.

Impact of incorporating substituents onto the P-o-anisyl groups of DiPAMP ligand on the rhodium(I)-catalyzed asymmetric hydrogenation of olefins

The introduction of 1,2-bis[(o-anisyl)-(phenyl)phosphino]ethane (DiPAMP) as a P-stereogenic ligand for rhodium(I)-catalyzed hydrogenation by Knowles et al. came after their evaluation of several diphosphines. However, no in-depth study was carried out on incorporating various substituents on its P-o-anisyl groups. In this work, we have prepared a large series of enantiopure and closely related DiPAMP analogues possessing various substituents (MeO, TMS, t-Bu, Ph, fused benzene ring) on the o-anisyl rings. The new ligands were evaluated in rhodium-catalyzed hydrogenation of several model substrates: methyl α-acetamidoacrylate, methyl (Z)-α-acetamidocinnamate, methyl (Z)-β-acetamidocrotonate, dimethyl itaconate, and atropic acid. They displayed enhanced activities and increased enantioselectivities, particularly the P-(2,3,4,5-tetra-MeO-C6H)-substituted ligand (4MeBigFUS). Interestingly enough, 88% ee was obtained in the hydrogenation of atropic acid using the Rh-(4MeBigFUS) catalyst under mild conditions (10 bar H2, room temperature) versus 7% ee using Rh-DiPAMP. Conversely, the ligand possessing P-(2,6-di-MeO-C6H3) groups proved to slow down considerably the hydrogenation. X-Ray structures of their corresponding Rh complexes are presented and discussed.

Synthesis and reactions of phosphine-boranes. Synthesis of new bidentate ligands with homochiral phosphine centers via optically pure phosphine-boranes

Secondary and tertiary phosphine-boranes were synthesized in one-pot from phosphine oxides or substituted chlorophosphines without isolation of the intermediate phosphines. Phosphine-boranes having a methyl group were metalated with sec-butyllithium. The generated carbanions reacted with alkyl halides or carbonyl compounds to yield various phosphine-borane derivatives. The carbanions underwent copper(II)-promoted oxidative coupling without impairment of the borane functionality. Secondary phosphine-boranes reacted with alkyl halides, aldehydes, or α,β-unsaturated carbonyl compounds to give phosphine-borane derivatives having a functional group. The boranato group of phosphine-boranes was removed in a stereospecific manner with retention of configuration by treatment with a large excess of amine such as morpholine. A new route to bidentate ligands with homochiral phosphine centers has been explored by utilizing these characteristic reactivities of phosphine-boranes. Thus, optically pure (S,S)-1,2-bis(o-anisylphenylphosphino)ethane, (R,R)-1,2-bis(tert-butylphenyl-phosphino)ethane, and (S,S)-1,4-bis(o-anisylphenylphosphino)butane have been synthesized via phosphine-boranes.