Mykura, Rory C.; Songara, Pradip; Luc, Eugenia; Rogers, Jack; Stammers, Ellie; Aggarwal, Varinder K. published an article in 2021. The article was titled 《Studies on the Lithiation, Borylation, and 1,2-Metalate Rearrangement of O-Cycloalkyl 2,4,6-Triisopropylbenzoates》, and you may find the article in Angewandte Chemie, International Edition.Electric Literature of C12H17BO2 The information in the text is summarized as follows:
A broad range of acyclic primary and secondary 2,4,6-triisopropylbenzoate (TIB) esters have been used in lithiation-borylation reactions, but cyclic TIB esters have not. Authors have studied the use of cyclic TIB esters in lithiation-borylation reactions and looked at the effect of ring size (3- → 6-membered rings) on the three key steps of the lithiation-borylation protocol: deprotonation, borylation and 1,2-metalate rearrangement. Although all rings sizes could be deprotonated, the cyclohexyl case was impractically slow, and the cyclopentyl example underwent α-elimination faster than deprotonation at -78° and so could not be used. Both cyclobutyl and cyclopropyl cases underwent rapid borylation, but only the cyclobutyl substrate underwent 1,2-metalate rearrangement. Thus, the cyclobutyl TIB ester occupies a “”Goldilocks zone,”” being small enough for deprotonation and large enough to enable 1,2-migration. The generality of the reaction was explored with a broad range of boronic esters.4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane(cas: 24388-23-6Electric Literature of C12H17BO2) was used in this study.
4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane(cas: 24388-23-6) can be used to prepare sulfinamide derivatives by reacting with diethylaminosulfur trifluoride (DAST) and potassium phenyltrifluoroborate.Electric Literature of C12H17BO2
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