BROWSE

Related Scientist

CCHF's photo.

CCHF
분자활성 촉매반응 연구단
more info

ITEM VIEW & DOWNLOAD

ZnMe2-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism

Cited 0 time in webofscience Cited 0 time in scopus
36 Viewed 0 Downloaded
Title
ZnMe2-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism
Author(s)
Woohyun Jo; Seung-yeol Baek; Chiwon Hwang; Joon Heo; Mu-Hyun Baik; Seung Hwan Cho
Subject
FREE REGIOSELECTIVE ALKYLATION, ; C-H FUNCTIONALIZATION, ; SELECTIVE ALKENYLATION, ; DIORGANOZINC COMPOUNDS, ; MOLECULAR CALCULATIONS, ; NITROGEN-HETEROCYCLES, ; FACILE SYNTHESIS, ; OXIDES, ; ARYLATION, ; METHYLATION
Publication Date
2020-07
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.30, pp.13235 - 13245
Publisher
AMER CHEMICAL SOC
Abstract
© 2020 American Chemical Society The regioselective, direct alkylation of electron-deficient N-heteroarenes is, in principle, a powerful and efficient way of accessing alkylated N-heteroarenes that are important core structures of many biologically active compounds and pharmaceutical agents. Herein, we report a ZnMe2-promoted, direct C2- or C4-selective primary and secondary alkylation of pyridines and quinolines using 1,1-diborylalkanes as alkylation sources. While substituted pyridines and quinolines exclusively afford C2-alkylated products, simple pyridine delivers C4-alkylated pyridine with excellent regioselectivity. The reaction scope is remarkably broad, and a range of C2- or C4-alkylated electron-deficient N-heteroarenes are obtained in good yields. Experimental and computational mechanistic studies imply that ZnMe2 serves not only as an activator of 1,1-diborylalkanes to generate (alpha-borylalkyl)methylalkoxy zincate, which acts as a Lewis acid to bind to the nitrogen atom of the heterocycles and controls the regioselectivity, but also as an oxidant for rearomatizing the dihydro-N-heteroarene intermediates to release the product
URI
https://pr.ibs.re.kr/handle/8788114/7746
DOI
10.1021/jacs.0c06827
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
Files in This Item:
There are no files associated with this item.

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