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KO tBu-Catalyzed 1,2-Silaboration of N-Heteroarenes to Access 2-Silylheterocycles: A Cooperative Model for the Regioselectivity

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Title
KO tBu-Catalyzed 1,2-Silaboration of N-Heteroarenes to Access 2-Silylheterocycles: A Cooperative Model for the Regioselectivity
Author(s)
Eunchan Jeong; Joon Heo; Seongho Jin; Dongwook Kim; Sukbok Chang
Publication Date
2022-01
Journal
ACS Catalysis, v.12, no.9, pp.4898 - 4905
Publisher
American Chemical Society
Abstract
© 2022 American Chemical Society.Reductive functionalization of N-heteroarenes offers a route to highly versatile heterocyclic synthons bearing multiple transformable groups. We present herein the development of KOtBu-catalyzed 1,2-silaboration of a broad range of N-heteroarenes, affording heterocyclic allylamines or enamines with the formation of a sp3 C2-Si bond. These labile compounds were isolated either as their N-acyl derivatives or as rearomatized 2-silyl-N-heteroarenes by the one-pot procedures. A model of the six-membered ion-pair complex was proposed to rationalize the observed 1,2-regioselectivity, wherein KOtBu catalyst plays an associative role in activating the substrate and silylborane reagent.
URI
https://pr.ibs.re.kr/handle/8788114/11477
DOI
10.1021/acscatal.2c01126
ISSN
2155-5435
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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