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

Autor: Trammel GL; Department of Chemistry, Indiana University, 800 E. Kirkwood Ave., Bloomington, IN, 47401, USA., Kannangara PB; Department of Chemistry, Indiana University, 800 E. Kirkwood Ave., Bloomington, IN, 47401, USA., Vasko D; Enamine Ltd., Chervonotkatska 60, 02094, Kyiv, Ukraine., Datsenko O; Enamine Ltd., Chervonotkatska 60, 02094, Kyiv, Ukraine., Mykhailiuk P; Enamine Ltd., Chervonotkatska 60, 02094, Kyiv, Ukraine.; Taras Shevchenko National University of Kyiv, Chemistry Department, Volodymyrska 64, 01601, Kyiv, Ukraine., Brown MK; Department of Chemistry, Indiana University, 800 E. Kirkwood Ave., Bloomington, IN, 47401, USA.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2022 Nov 14; Vol. 61 (46), pp. e202212117. Date of Electronic Publication: 2022 Oct 17.
DOI: 10.1002/anie.202212117
Abstrakt: 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.
(© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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