844645-03-0

Basic information

• Product Name: (R)-1-(3-bromophenyl)-1-(trichlorosilyl)ethane
• Synonyms: (R)-1-(3-bromophenyl)-1-(trichlorosilyl)ethane
• CAS NO: 844645-03-0
• Molecular Weight: 318.5
• Mol File: 844645-03-0.mol

Chemical Properties

• CAS DataBase Reference: (R)-1-(3-bromophenyl)-1-(trichlorosilyl)ethane(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(3-bromophenyl)-1-(trichlorosilyl)ethane(844645-03-0)
• EPA Substance Registry System: (R)-1-(3-bromophenyl)-1-(trichlorosilyl)ethane(844645-03-0)

Safety Data

• Hazardous Substances Data: 844645-03-0(Hazardous Substances Data)

Upstream product

• 2039-86-3 3-bromostyrene 

Downstream Products

• 52780-14-0 (R)-1-(3-bromophenyl)ethanol 

Relevant articles and documents

Asymmetric palladium-catalyzed hydrosilylation of styrenes using efficient chiral spiro phosphoramidite ligands

Asymmetric hydrosilylation of styrene derivatives with trichlorosilane in the presence of palladium complexes of chiral spiro phosphoramidites provided 1-aryl-1-silylalkanes as single regioisomers in high yields, which have been oxidized with hydrogen peroxide to give the corresponding chiral alcohols in up to 99.1% ee.

Asymmetric hydrosilylation of styrenes catalyzed by palladium-MOP complexes: Ligand modification and mechanistic studies

In the palladium-catalyzed asymmetric hydrosilylation of styrene (3a) with trichlorosilane, several chiral monophosphine ligands, (R)-2-diarylphosphino-1,1′-binaphthyls (2a-g), were examined for their enantioselectivity. The highest enantioselectivity was observed in the reaction with (R)-2-bis[3,5-bis(trifluoromethyl)phenyl]phosphino-1, 1′-binaphthyl (2g), which gave (S)-1-phenylethanol (5a) of 98% ee after oxidation of the hydrosilylation product, 1-phenyl-1-(trichlorosilyl)ethane (4a). The palladium complex of 2g also efficiently catalyzed the asymmetric hydrosilylation of substituted styrenes on the phenyl ring or at the β position to give the corresponding chiral benzylic alcohols of over 96% ee. Deuterium-labeling studies on the hydrosilylation of regiospecifically deuterated styrene revealed that β-hydrogen elimination from 1-phenylethyl(silyl)palladium intermediate is very fast compared with reductive elimination giving hydrosilylation product when ligand 2g is used. The reaction of o-allylstyrene (9) with trichlorosilane catalyzed by (R)-2g/Pd gave (1S,2R)-1-methyl-2-(trichlorosilylmethyl)indan (10) (91% ee) and (S)-1-(2-(propenyl)phenyl)-1-trichlorosilylethanes (11a and 11b) (95% ee). On the basis of their opposite configurations at the benzylic position, a rationale for the high enantioselectivity of ligand 2g is proposed.