Tail-To-Tail Stereoselective Dimerization of Acrylate Derivatives via Iridium-Catalyzed Vinylic sp2 C−H Activation

Masafumi Kojima; Mio Sasaki; Mamoru Ito; Takanori Shibata

doi:10.1002/adsc.202200047

Tail-To-Tail Stereoselective Dimerization of Acrylate Derivatives via Iridium-Catalyzed Vinylic sp² C−H Activation

Masafumi Kojima, Mio Sasaki, Mamoru Ito, Takanori Shibata^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

2 Citations (Scopus)

Abstract

We describe a cationic Ir-catalyzed tail-to-tail dimerization of aryl acrylates starting from vinylic sp² C−H activation, which gives industrially useful adipic acid ester derivatives in high yields. We further expanded the reaction to an enantioselective dimerization using aryl methacrylates and achieved the first example of catalytic asymmetric dimerization of acrylate derivatives. (Figure presented.).

Original language	English
Pages (from-to)	1666-1670
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	364
Issue number	10
DOIs	https://doi.org/10.1002/adsc.202200047
Publication status	Published - 2022 May 17

Keywords

acrylates
dimerization
enantioselective self-coupling
iridium catalyst
vinylic sp C−H bond activation

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.202200047

Cite this

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title = "Tail-To-Tail Stereoselective Dimerization of Acrylate Derivatives via Iridium-Catalyzed Vinylic sp2 C−H Activation",

abstract = "We describe a cationic Ir-catalyzed tail-to-tail dimerization of aryl acrylates starting from vinylic sp2 C−H activation, which gives industrially useful adipic acid ester derivatives in high yields. We further expanded the reaction to an enantioselective dimerization using aryl methacrylates and achieved the first example of catalytic asymmetric dimerization of acrylate derivatives. (Figure presented.).",

keywords = "acrylates, dimerization, enantioselective self-coupling, iridium catalyst, vinylic sp C−H bond activation",

author = "Masafumi Kojima and Mio Sasaki and Mamoru Ito and Takanori Shibata",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number 19 K05485. We thank Dr. Natsuhiko Sugimura (Materials Characterization Central Laboratory, Waseda University) for his support to reaction mechanism analysis. Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

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T1 - Tail-To-Tail Stereoselective Dimerization of Acrylate Derivatives via Iridium-Catalyzed Vinylic sp2 C−H Activation

AU - Kojima, Masafumi

AU - Sasaki, Mio

AU - Ito, Mamoru

AU - Shibata, Takanori

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number 19 K05485. We thank Dr. Natsuhiko Sugimura (Materials Characterization Central Laboratory, Waseda University) for his support to reaction mechanism analysis. Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2022/5/17

Y1 - 2022/5/17

N2 - We describe a cationic Ir-catalyzed tail-to-tail dimerization of aryl acrylates starting from vinylic sp2 C−H activation, which gives industrially useful adipic acid ester derivatives in high yields. We further expanded the reaction to an enantioselective dimerization using aryl methacrylates and achieved the first example of catalytic asymmetric dimerization of acrylate derivatives. (Figure presented.).

AB - We describe a cationic Ir-catalyzed tail-to-tail dimerization of aryl acrylates starting from vinylic sp2 C−H activation, which gives industrially useful adipic acid ester derivatives in high yields. We further expanded the reaction to an enantioselective dimerization using aryl methacrylates and achieved the first example of catalytic asymmetric dimerization of acrylate derivatives. (Figure presented.).

KW - acrylates

KW - dimerization

KW - enantioselective self-coupling

KW - iridium catalyst

KW - vinylic sp C−H bond activation

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