196403-59-5

Upstream product

• 3609-53-8 methyl 4-acetylbenzoate 
• 199188-36-8 4-(1-(trifluoromethanesulfonyloxy)vinyl)benzoic acid methyl ester 
• 199188-35-7 Trifluoro-methanesulfonic acid 5,5,8,8-tetramethyl-3-trifluoromethyl-5,6,7,8-tetrahydro-naphthalen-2-yl ester 
• 199188-34-6 Trifluoro-methanesulfonic acid 3-iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl ester 
• 199188-31-3 6-iodo-7-methoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene 
• 170100-73-9 2-bromo-3-methoxy-5,5,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene 
• 199188-33-5 3-iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol 
• 578-57-4 2-bromoanisole 
• 6223-78-5 2,5-dichloro-2,5-dimethyl hexane 

Relevant academic research and scientific papers

A Suzuki coupling approach to trifluoromethyl derivative of targretin (LGD 1069)

The palladium-catalyzed Suzuki coupling reaction σ-trinuoromethylated arylboronic acid 4 and vinyl triflate 5 provided the trifluoromethyl derivative of Targretin (LGD1069).

First synthesis of ortho-trifluoromethylated aryl triflates

An efficient method for the preparation of trifluoromethylated aryl triflates (trifluoromethanesulfonates) has been developed. Treatment of 2-iodophenol with trifluoromethanesulfonic anhydride in the presence of triethylamine gives triflate 3. Then, reaction of compound 3 with FSO2CF2CO2Me and CuI in DMF-HMPA affords trifluoromethylated aryl triflate 2. This reaction sequence is also successful for meta- and para-trifluoromethylated aryl triflates. Based on this methodology, the trifluoromethylated aryl triflate 11, a key intermediate for the preparation of the conformationally restricted retinoid 8 containing a trifluoromethyl group, has been synthesized. The cross-coupling of aryl triflate 11 with vinylstannane 17 under palladium catalysis provides compound 18, the methyl ester of retinoid 8, in moderate yield.