Iron-Catalyzed Directed C−H Silylation of Pivalophenone N−H Imines

Wengang Xu; Jie Hui Pek; Naohiko Yoshikai

doi:10.1002/ajoc.201800171

Iron-Catalyzed Directed C−H Silylation of Pivalophenone N−H Imines

Wengang Xu, Jie Hui Pek, Naohiko Yoshikai

PHA - Molecular Pharmaceutical Science

Nanyang Technological University

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

10 Citations (Scopus)

Abstract

An iron-catalyzed, N−H imine-directed arene C−H silylation reaction with hydrosilane has been achieved. Pivalophenone N−H imine undergoes ortho C−H silylation with triethylsilane in the presence of [Fe₃(CO)₁₂] as a catalyst and norbornene as a hydrogen acceptor. The product can be readily transformed into ortho-silylated benzonitrile via conversion of the imine functionality to a cyano group under peroxide photolysis.

Original language	English
Pages (from-to)	1351-1354
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	7
Issue number	7
DOIs	https://doi.org/10.1002/ajoc.201800171
Publication status	Published - 2018 Jul

Keywords

C−H activation
hydrosilane
imine
iron
synthetic methods

Access to Document

10.1002/ajoc.201800171

Cite this

@article{8ea7a96445cc4fd3a40c55722415f7d3,

title = "Iron-Catalyzed Directed C−H Silylation of Pivalophenone N−H Imines",

abstract = "An iron-catalyzed, N−H imine-directed arene C−H silylation reaction with hydrosilane has been achieved. Pivalophenone N−H imine undergoes ortho C−H silylation with triethylsilane in the presence of [Fe3(CO)12] as a catalyst and norbornene as a hydrogen acceptor. The product can be readily transformed into ortho-silylated benzonitrile via conversion of the imine functionality to a cyano group under peroxide photolysis.",

keywords = "C−H activation, hydrosilane, imine, iron, synthetic methods",

author = "Wengang Xu and Pek, {Jie Hui} and Naohiko Yoshikai",

note = "Funding Information: This work was supported by Ministry of Education (Singapore) and Nanyang Technological University (RG3/15, RG114/15, and MOE2016-T2-2–043) and JST, CREST. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = jul,

doi = "10.1002/ajoc.201800171",

language = "English",

volume = "7",

pages = "1351--1354",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

number = "7",

}

TY - JOUR

T1 - Iron-Catalyzed Directed C−H Silylation of Pivalophenone N−H Imines

AU - Xu, Wengang

AU - Pek, Jie Hui

AU - Yoshikai, Naohiko

N1 - Funding Information: This work was supported by Ministry of Education (Singapore) and Nanyang Technological University (RG3/15, RG114/15, and MOE2016-T2-2–043) and JST, CREST. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/7

Y1 - 2018/7

N2 - An iron-catalyzed, N−H imine-directed arene C−H silylation reaction with hydrosilane has been achieved. Pivalophenone N−H imine undergoes ortho C−H silylation with triethylsilane in the presence of [Fe3(CO)12] as a catalyst and norbornene as a hydrogen acceptor. The product can be readily transformed into ortho-silylated benzonitrile via conversion of the imine functionality to a cyano group under peroxide photolysis.

AB - An iron-catalyzed, N−H imine-directed arene C−H silylation reaction with hydrosilane has been achieved. Pivalophenone N−H imine undergoes ortho C−H silylation with triethylsilane in the presence of [Fe3(CO)12] as a catalyst and norbornene as a hydrogen acceptor. The product can be readily transformed into ortho-silylated benzonitrile via conversion of the imine functionality to a cyano group under peroxide photolysis.

KW - C−H activation

KW - hydrosilane

KW - imine

KW - iron

KW - synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=85049841347&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85049841347&partnerID=8YFLogxK

U2 - 10.1002/ajoc.201800171

DO - 10.1002/ajoc.201800171

M3 - Article

AN - SCOPUS:85049841347

SN - 2193-5807

VL - 7

SP - 1351

EP - 1354

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 7

ER -

Iron-Catalyzed Directed C−H Silylation of Pivalophenone N−H Imines

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this