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Sardini, Stephen R.; Lambright, Alison L.; Trammel, Grace L.; Omer, Humair M.; Liu, Peng; Brown, M. Kevin (, Journal of the American Chemical Society)
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Trammel, Grace L.; Kannangara, Prashansa B.; Vasko, Dmytro; Datsenko, Oleksandr; Mykhailiuk, Pavel; Brown, M. Kevin (, Angewandte Chemie International Edition)Abstract Two catalytic systems have been developed for the arylboration of endocyclic enecarbamates to deliver synthetically versatile borylated saturated N‐heterocycles in good regio‐ and diastereoselectivities. A Cu/Pd dual catalytic reaction enables the synthesis of borylated, α‐arylated azetidines, while a Ni‐catalysed arylboration reaction efficiently functionalizes 5‐, 6‐, and 7‐membered enecarbamates. In the case of the Cu/Pd‐system, a remarkable additive effect was identified that allowed for broader scope. The products are synthetically useful, as demonstrated by manipulations of the boronic ester to access biologically active compounds.more » « less
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