Nondissociative chain walking as a strategy in catalytic organic synthesis

Takuya Kochi; Shota Kanno; Fumitoshi Kakiuchi

doi:10.1016/j.tetlet.2019.07.029

Nondissociative chain walking as a strategy in catalytic organic synthesis

Takuya Kochi, Shota Kanno, Fumitoshi Kakiuchi

Department of Chemistry

Research output: Contribution to journal › Review article › peer-review

43 Citations (Scopus)

Abstract

“Nondissociative” chain walking is a mechanism where an alkylmetal species undergoes rapid β-hydride elimination and reinsertion to move the metal center along the alkyl chain without dissociating an alkene intermediate during the migration process. This digest summarizes the unique characteristics of the nondissociative chain walking mechanism compared to the stepwise alkene isomerization mechanism and their use in catalytic organic synthesis.

Original language	English
Article number	150938
Journal	Tetrahedron Letters
Volume	60
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2019.07.029
Publication status	Published - 2019 Sept 12

Keywords

Isomerization
Metal catalysis
Nondissociative chain walking
Remote functionalization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2019.07.029

Cite this

@article{88c5ca3fcbdf4ffc929dcc978abf36b3,

title = "Nondissociative chain walking as a strategy in catalytic organic synthesis",

abstract = "“Nondissociative” chain walking is a mechanism where an alkylmetal species undergoes rapid β-hydride elimination and reinsertion to move the metal center along the alkyl chain without dissociating an alkene intermediate during the migration process. This digest summarizes the unique characteristics of the nondissociative chain walking mechanism compared to the stepwise alkene isomerization mechanism and their use in catalytic organic synthesis.",

keywords = "Isomerization, Metal catalysis, Nondissociative chain walking, Remote functionalization",

author = "Takuya Kochi and Shota Kanno and Fumitoshi Kakiuchi",

note = "Funding Information: This work was supported, in part, by JSPS KAKENHI Grant Numbers JP18H01985 (Grant-in-Aid for Scientific Research (B)), JP15KT0069 (Grant-in-Aid for Scientific Research (B)) and JP18H04271 (Precisely Designed Catalysts with Customized Scaffolding) and the Asahi Glass Foundation . Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = sep,

day = "12",

doi = "10.1016/j.tetlet.2019.07.029",

language = "English",

volume = "60",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "37",

}

TY - JOUR

T1 - Nondissociative chain walking as a strategy in catalytic organic synthesis

AU - Kochi, Takuya

AU - Kanno, Shota

AU - Kakiuchi, Fumitoshi

N1 - Funding Information: This work was supported, in part, by JSPS KAKENHI Grant Numbers JP18H01985 (Grant-in-Aid for Scientific Research (B)), JP15KT0069 (Grant-in-Aid for Scientific Research (B)) and JP18H04271 (Precisely Designed Catalysts with Customized Scaffolding) and the Asahi Glass Foundation . Publisher Copyright: © 2019 Elsevier Ltd

PY - 2019/9/12

Y1 - 2019/9/12

N2 - “Nondissociative” chain walking is a mechanism where an alkylmetal species undergoes rapid β-hydride elimination and reinsertion to move the metal center along the alkyl chain without dissociating an alkene intermediate during the migration process. This digest summarizes the unique characteristics of the nondissociative chain walking mechanism compared to the stepwise alkene isomerization mechanism and their use in catalytic organic synthesis.

AB - “Nondissociative” chain walking is a mechanism where an alkylmetal species undergoes rapid β-hydride elimination and reinsertion to move the metal center along the alkyl chain without dissociating an alkene intermediate during the migration process. This digest summarizes the unique characteristics of the nondissociative chain walking mechanism compared to the stepwise alkene isomerization mechanism and their use in catalytic organic synthesis.

KW - Isomerization

KW - Metal catalysis

KW - Nondissociative chain walking

KW - Remote functionalization

UR - http://www.scopus.com/inward/record.url?scp=85071056808&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85071056808&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2019.07.029

DO - 10.1016/j.tetlet.2019.07.029

M3 - Review article

AN - SCOPUS:85071056808

SN - 0040-4039

VL - 60

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

M1 - 150938

ER -

Nondissociative chain walking as a strategy in catalytic organic synthesis

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this