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Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N-Heterocycles.

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.

SUBMITTER: Trammel GL

PROVIDER: S-EPMC9643676 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N-Heterocycles.

Trammel Grace L GL Kannangara Prashansa B PB Vasko Dmytro D Datsenko Oleksandr O Mykhailiuk Pavel P Brown M Kevin MK

Angewandte Chemie (International ed. in English) 20221017 46

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 bro ...[more]

PMID: 36250954

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