Ir-Catalyzed Remote Functionalization by the Combination of Deconjugative Chain-Walking and C-H Activation Using a Transient Directing Group

King Hung Nigel Tang; Kanako Uchida; Kazuki Nishihara; Mamoru Ito; Takanori Shibata

doi:10.1021/acs.orglett.1c04321

Ir-Catalyzed Remote Functionalization by the Combination of Deconjugative Chain-Walking and C-H Activation Using a Transient Directing Group

King Hung Nigel Tang, Kanako Uchida, Kazuki Nishihara, Mamoru Ito, Takanori Shibata^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

An Ir-catalyzed reaction of N-benzylideneanilines with functionalized alkenes such as α,β-unsaturated esters gave ortho-substituted benzaldehyde derivatives with a functional group at the remote position after acidic treatment. The present transformation involves deconjugative long-range isomerization (chain-walking) up to 11 times and C-H activation using an imino group as a transient directing group.

Original language	English
Pages (from-to)	1313-1317
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.1c04321
Publication status	Published - 2022 Feb 18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.1c04321

Cite this

@article{9d7b828422da4c01bc2a56f87cb9f436,

title = "Ir-Catalyzed Remote Functionalization by the Combination of Deconjugative Chain-Walking and C-H Activation Using a Transient Directing Group",

abstract = "An Ir-catalyzed reaction of N-benzylideneanilines with functionalized alkenes such as α,β-unsaturated esters gave ortho-substituted benzaldehyde derivatives with a functional group at the remote position after acidic treatment. The present transformation involves deconjugative long-range isomerization (chain-walking) up to 11 times and C-H activation using an imino group as a transient directing group.",

author = "Tang, {King Hung Nigel} and Kanako Uchida and Kazuki Nishihara and Mamoru Ito and Takanori Shibata",

note = "Funding Information: This work was supported by Waseda University Grant for Special Research Projects and JST SPRING, Grant Number JPMJSP2128. Publisher Copyright: {\textcopyright} 2022 American Chemical Society",

year = "2022",

month = feb,

day = "18",

doi = "10.1021/acs.orglett.1c04321",

language = "English",

volume = "24",

pages = "1313--1317",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Ir-Catalyzed Remote Functionalization by the Combination of Deconjugative Chain-Walking and C-H Activation Using a Transient Directing Group

AU - Tang, King Hung Nigel

AU - Uchida, Kanako

AU - Nishihara, Kazuki

AU - Ito, Mamoru

AU - Shibata, Takanori

N1 - Funding Information: This work was supported by Waseda University Grant for Special Research Projects and JST SPRING, Grant Number JPMJSP2128. Publisher Copyright: © 2022 American Chemical Society

PY - 2022/2/18

Y1 - 2022/2/18

N2 - An Ir-catalyzed reaction of N-benzylideneanilines with functionalized alkenes such as α,β-unsaturated esters gave ortho-substituted benzaldehyde derivatives with a functional group at the remote position after acidic treatment. The present transformation involves deconjugative long-range isomerization (chain-walking) up to 11 times and C-H activation using an imino group as a transient directing group.

AB - An Ir-catalyzed reaction of N-benzylideneanilines with functionalized alkenes such as α,β-unsaturated esters gave ortho-substituted benzaldehyde derivatives with a functional group at the remote position after acidic treatment. The present transformation involves deconjugative long-range isomerization (chain-walking) up to 11 times and C-H activation using an imino group as a transient directing group.

UR - http://www.scopus.com/inward/record.url?scp=85124850390&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85124850390&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c04321

DO - 10.1021/acs.orglett.1c04321

M3 - Article

C2 - 35139636

AN - SCOPUS:85124850390

SN - 1523-7060

VL - 24

SP - 1313

EP - 1317

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Ir-Catalyzed Remote Functionalization by the Combination of Deconjugative Chain-Walking and C-H Activation Using a Transient Directing Group

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this