BROWSE

Related Scientist

Researcher

분자활성 촉매반응 연구단
분자활성 촉매반응 연구단
more info

Delineating Physical Organic Parameters in Site-Selective C-H Functionalization of Indoles

Cited 0 time in webofscience Cited 0 time in scopus
47 Viewed 16 Downloaded
Title
Delineating Physical Organic Parameters in Site-Selective C-H Functionalization of Indoles
Author(s)
Youyoung Kim; Yoonsu Park; Sukbok Chang
Publication Date
2018-06
Journal
ACS CENTRAL SCIENCE, v.4, no.6, pp.768 - 775
Publisher
AMER CHEMICAL SOC
Abstract
Site-selective C-H functionalization is a great challenge in homogeneous transition-metal catalysis. Herein, we present a physical organic approach to delineate the origin of regioselective amidation of N-acylindoles through Ir(III) catalysis. Bulkiness of N-directing groups of indole substrates and electronics of carboxylate additives were identified as two major factors in controlling C2 and C7 selectivity, and their microscopic mechanisms were studied with DFT-based transition state analysis. Computational insights led us to interrogate a linear free energy relationship, and parametrization of molecular determinants enabled the establishment of an intuitive yet robust statistical model that correlates an extensive number of validation data points in high accuracy. This mechanistic investigation eventually allowed the development of a new C2 amidation and alkenylation protocol of indoles, which affords the exclusive functionalization at the C2 position with up to >70:1 selectivity. © 2018 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/4980
ISSN
2374-7943
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
acscentsci.8b00264.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