Iridium-catalyzed selective 1,2-hydrosilylation of N-heterocycles

Cited 7 time in webofscience Cited 0 time in scopus
176 Viewed 4 Downloaded
Title
Iridium-catalyzed selective 1,2-hydrosilylation of N-heterocycles
Author(s)
Jinseong Jeong; Sehoon Park; Sukbok Chang
Publication Date
2016-08
Journal
CHEMICAL SCIENCE, v.7, no.8, pp.5362 - 5370
Publisher
ROYAL SOC CHEMISTRY
Abstract
A silylene-bridged Ir dimer in situ generated from [Ir(coe)2Cl]2 and Et2SiH2 was found to catalyze the hydrosilylation of N-heteroaromatics to furnish dearomatized azacyclic products with high activity (up to 1000 TONs), excellent selectivity, and good functional group tolerance. The substrate scope was highly broad, including (iso)quinolines, substituted pyridines, pyrimidines, pyrazines, deazapurines, triazines, and benzimidazoles. Mechanistic studies such as a kinetic profile, rate-order assessment, and investigation of the electronic substituent effects on the initial rates were performed to access the detailed pathways. One pathway is proposed to involve an intramolecular insertion of the CN moiety of the substrates into the Ir-H bond of a resting species to form an Ir-amido silyl intermediate, followed by reductive elimination. The synthetic utility was proven by successful application to cinchona alkaloids, and facile post-synthetic transformations of the 1,2-dihydroquinoline products. © 2016 The Royal Society of Chemistry
URI
https://pr.ibs.re.kr/handle/8788114/3285
ISSN
2041-6520
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
Iridium-catalyzed selective 1,2-hydrosilylation of N-heterocycles.pdfDownload

qrcode

  • facebook

    twitter

  • Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.
해당 아이템을 이메일로 공유하기 원하시면 인증을 거치시기 바랍니다.

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

Browse