Products Cited in Publications Worldwide Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N-Heterocycles

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

Grace L. Trammel; Prashansa B. Kannangara; Dmytro Vasko; Oleksandr Datsenko; Pavel Mykhailiuk; M. Kevin Brown

DOI: PMID:

Abstract

Two catalytic systems have been developed for the arylboration of endocyclic enecarbamates to deliver synthetically versatile borylated saturated Nheterocycles 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/Pdsystem, 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.

Keywords

Alkene ; Arylation ; Boron ; Cross Coupling ; Heterocycle

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