170647-24-2

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 173300-94-2 2-(naphthalen-1-yl)benzene-1,3-diol 
• 173300-93-1 1-(2,6-dimethoxyphenyl)naphthalene 
• 16932-45-9 1-bromo-2,6-dimethoxybenzene 
• 151-10-0 1,3-Dimethoxybenzene 
• 13922-41-3 1-Naphthylboronic acid 

Downstream Products

• 178099-19-9 Trifluoro-methanesulfonic acid 3-hept-1-ynyl-2-naphthalen-1-yl-phenyl ester 
• 170647-29-7 (S)-(-)-2-naphthyl-3-trifluoromethanesulfonyloxybiphenyl 

Relevant academic research and scientific papers

Enantioposition-selective arylation of biaryl ditriflates by palladium- catalyzed asymmetric Grignard cross-coupling

Asymmetric cross-coupling of achiral biaryl ditriflates with aryl Grignard reagents in the presence of 1 equiv of lithium bromide and 5 tool % of palladium complex PdCl2[(S)-alaphos], where alaphos stands for (2- dimethylamino)propyldiphenylphosphine, gave axially chiral monophenylation products with high enantioposition-selectivity. The remaining triflate group in the monophenylation products was substituted with carboxyl and diphenylphosphino groups through palladium-catalyzed carbonylation and diphenylphosphinylation, respectively.

Enantioposition-selective alkynylation of biaryl ditriflates by palladium-catalyzed asymmetric cross-coupling

Asymmetric cross-coupling of prochiral biaryl ditriflate, 1-[2,6-bis[[(trifluoromethyl)sulfonyl]oxy]phenyl]naphthalene (1) or 1,3-bis[[(trifluoromethyl)sulfonyl]oxy]-2-(biphenyl-2-yl)benzene (4) with triphenylsilylethynylmagnesium bromide in the presence of lithium bromide and 5 mol% of palladium catalyst, PdCl2[(S)-Alaphos], proceeded with high enantioposition selectivity to give high yields of the corresponding axially chiral monoalkynylated biaryls, 2a or 2d, of high enantiomeric purity (up to >99% ee).