1079366-57-6

Upstream product

• 402-45-9 4-hydroxybenzotrifluoride 
• 10294-34-5 boron trichloride 

Downstream Products

• 229007-83-4 ethyl 7-(4-trifluoromethylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate 
• 1079366-97-4 3-phenyl-3-(4-(trifluoromethyl)phenoxy)-N-(4-methylphenylsulfonyl)propanamine 
• 180961-71-1 (R)-3-phenyl-3-(4-(trifluoromethyl)phenoxy)propan-1-ol 

Relevant academic research and scientific papers

Probing substituent effects on the activation of H2 by phosphorus and boron frustrated Lewis pairs

The impact of substituent changes on phosphorus and boron-containing frustrated Lewis pairs (FLPs) has been examined. The phosphites (RO) 3P R = Me, Ph form classical Lewis acid-base adducts of the formula (RO)3PB(C6F5)3 R = Me 1; R = Ph 2, whereas P(O-2,4-tBu2C6H3) 3 and P(O-2,6-Me2C6H3)3 generate FLPs. Nonetheless, these latter combinations do not react with H 2. The more basic phosphinite tBu2POR, R = tBu 3 reacts with B(C6F5)3 to give (tBu2(H)PO) B(C6F5)36. The related species tBu 2POR, R = Ph 4; 2,6-Me2C6H35 showed no reaction with B(C6F5)3 but the FLPs react under H2 (4 atm) to give [tBu2P(OR)H][HB(C 6F5)3] R = Ph 7 and 2,6-Me2C 6H38. Similarly, tBu2PCl in combination with B(C6F5)3, generates an FLP that upon addition of H2, gives [tBu2PH2][ClB(C6F 5)3] 9 albeit in low yield. The diborane 1,4-(C 6F5)2B(C6F4)B(C 6F5)2 in combination with either tBu 3P or (C6H2Me3)3P generates FLPs that react with H2 to give [R3PH] 2[1,4-(C6F5)2HB(C6F 4)BH(C6F5)2] (R = tBu 11, C 6H2Me312). Similarly PhB(C6F 5)2 and tBu3P react with H2 giving [tBu3PH][HBPh(C6F5)2] 13. The combination of B(OC6F5)3 and PtBu3 also generate an FLP which reacts with H2 to give [HPtBu 3][B(OC6F5)4] 14, the product of substituent redistribution. The boronic esters, (C6H 4O2)BC6F515, (C6H 3FO2)BC6F516 and (C 6F4O2)BC6F517, and the borate esters B(OC6H3(CF3)2) 318, B(OC6H2F3)319 and B(OC6H4CF3)320 were prepared and shown to generate FLPs with tBu3P or (C6H 2Me3)3P. Nonetheless, no reaction with H 2 was observed for 15-17. Collectively these data suggest that there is a threshold of combined Lewis acidity and basicity that is required to effect the splitting of H2.

Regio- and stereoselective ring opening of enantiomerically enriched 2-aryl oxetanes and 2-aryl azetidines with aryl borates

(Chemical Equation Presented) The regioselective ring opening of 2-aryl-substituted four-membered heterocyclic rings with phenols, including catechol, was achieved by the use of aryl borates in mild and neutral reaction conditions without the aid of any transition metal catalysts. While β-alkyl azetidines were found not to be reactive, optically active N-tosyl azetidines gave the corresponding β-aryloxy amines in a racemic form, thus indicating the considerable carbocationic character of the transition state. The introduction of a hydroxyl group in the azetidine ring (i.e., an azetidinol), able to anchor the aryl borate and to direct the subsequent nucleophilic delivery, was shown to determine the ring-opening process with predominant inversion of configuration. When enantiomerically enriched 2-aryl oxetanes were used, the reduced extent of racemization observed (up to 93:7 er) was rationalized by an intramolecular delivery through a six-membered transition state, giving β-aryloxy alcohols with a predominant retention of configuration (i.e., a syn-stereoselective ring opening). The aryloxy alcohols obtained, endowed with suitable functionalities, can be cyclized to give access to enantiomerically enriched 2-aryl-1,5-benzodioxepins.