1246888-90-3

Usage

Reaction

Ligand/palladium catalyst for general and sterically demanding Suzuki-Miyaura cross-coupling reactions. Ligand/palladium catalyst for sterically demanding Buchwald-Hartwig amination. Ligand/palladium catalyst for asymmetric Suzuki-Miyaura cross-coupling reactions. Ligand/nickel catalyst for asymmetric intramolecular reductive cyclization Ligand/rhodium catalyst for asymmetric hydroboration

Upstream product

• 1246888-86-7 3-(t-butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole-3-oxide 
• 1338453-99-8 (S)-3-(tert-butyl)-4-(2,6-dimethoxyphenyl)-2H-benzo[d][1,3]oxaphosphole 3-oxide 
• 1338453-90-9 (S)-3-(tert-butyl)-4-hydroxy-2H-benzo[d][1,3]oxaphosphole 3-oxide 
• 1202032-99-2 (R)-3-(tert-butyl)-3-oxido-2H-benzo[d][1,3]oxaphosphol-4-yl trifluoromethanesulfonate 
• 151-10-0 1,3-Dimethoxybenzene 
• 23112-96-1 (2,6-dimethoxyphenyl)boronic acid 
• 1373432-34-8 (R)-3-(tert-butyl)-4-(2,6-dimethoxyphenyl)-2,3 dihydrobenzo[d][1,3]oxaphosphole-3-oxide 
• 1338453-95-4 (S)-3-tert-butyl-2,3-dihydrobenzo[d][1,3]oxaphosphol-4-yl trifluoromethanesulfonate oxide 
• 1246888-79-8 3-tert-butyl-3-oxido-2,3-dihydrobenzo[d][1,3]oxaphosphol-4-yl trifluoromethanesulfonate 
• 1202032-95-8 racemic 3-tert-butyl-2,3-dihydrobenzo[d][1,3]oxaphosphol-4-ol oxide 
• 2785-97-9 (2,6-dimethoxyphenyl)lithium 
• 1202032-91-4 tert-butyl(2,6-dimethoxyphenyl)(methyl)phosphine oxide 

Relevant academic research and scientific papers

Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki-Miyaura and Negishi Cross-Coupling Reactions for Tetra- ortho-Substituted Biaryl Synthesis

Metal-catalyzed cross-coupling reactions are extensively employed in both academia and industry for the synthesis of biaryl derivatives for applications to both medicine and material science. Application of these methods to prepare tetra-ortho-substituted

HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature

The new monophosphine ligand HandaPhos has been identified such that when complexed in a 1:1 ratio with Pd(OAc)2, enables Pd-catalyzed cross-couplings to be run using ≤1000 ppm of this pre-catalyst. Applications to Suzuki-Miyaura reactions involving highly funtionalized reaction partners are demonstrated, all run using environmentally benign nanoreactors in water at ambient temperatures.

Synthesis of P-Chiral Dihydrobenzooxaphospholes Through Negishi Cross-Coupling

An efficient Negishi cross-coupling was developed for the synthesis of the biaryl axes present in useful P-chiral dihydrobenzooxaphosphole ligands. This approach has allowed for the synthesis of new derivatives of these ligands that were not accessible by the previous route employing Suzuki-Miyaura cross-coupling. The use of Pd2(dba)3/BI-DIME as the catalyst system affords the desired biaryl compounds in good yields with excellent rates and with catalyst loadings as low as 0.25 mol %.

Ligand-accelerated stereoretentive Suzuki-Miyaura coupling of unprotected 3,3′-dibromo-BINOL

An efficient synthesis of the enantiomerically pure 3,3′-bis-arylated BINOL derivatives is accomplished through the palladium-catalyzed Suzuki-Miyaura coupling of the unprotected 3,3′-dibromo-BINOL with complete retention of enantiopurity. The active cata

Synthesis of chiral α-amino tertiary boronic esters by enantioselective hydroboration of α-arylenamides

The rhodium-catalyzed asymmetric hydroboration of α-arylenamides with BI-DIME as the chiral ligand and (Bpin)2 as the reagent yields for the first time a series of α-amino tertiary boronic esters in good yields and excellent enantioselectivities (up to 99% ee).

Asymmetric ring-opening of oxabenzonorbornadiene with amines promoted by a chiral iridium-monophosphine catalyst

A new iridium-monophosphine catalyst is found to be efficient for asymmetric ring-opening of benzonorbornadiene with amines, providing a series of chiral substituted dihydronaphthalenes in high yields (up to 98%) and excellent enantioselectivities (>99%).

Efficient chiral monophosphorus ligands for asymmetric Suzuki-Miyaura coupling reactions

A series of novel P-chiral monophosphorus ligands exhibit efficiency in asymmetric Suzuki-Miyaura coupling reactions, enabling the construction of an array of chiral biaryl products in high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. The carbonyl-benzooxazolidinone moiety in these chiral biaryl products allows facile derivatization for further synthetic applications. A computational study has revealed that a π-π interaction between the two coupling partners can enhance the enantioselectivity of the coupling reaction.

MONOPHOSPHORUS LIGANDS AND THEIR USE IN CROSS-COUPLING REACTIONS

Phosphine ligands of the formula Ia, IB and mixtures thereof.

A general and special catalyst for suzuki-miyaura coupling processes

(Figure Presented) Biaryl monophosphorus ligands containing a 2,3-dihydrobenzo[d][1,3]oxaphosphole framework are highly effective for the palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of a wide range of substrates. Ligand 1 has demonstrated excellent performance for coupling reactions of extremely hindered arylboronic acids.