Nondissociative chain walking as a strategy in catalytic organic synthesis

Research output: Contribution to journalReview article

2 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 languageEnglish
Article number150938
JournalTetrahedron Letters
Volume60
Issue number37
DOIs
Publication statusPublished - 2019 Sep 12

Fingerprint

Synthetic Chemistry Techniques
Alkenes
Walking
Isomerization
Hydrides
Metals

Keywords

  • Isomerization
  • Metal catalysis
  • Nondissociative chain walking
  • Remote functionalization

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Nondissociative chain walking as a strategy in catalytic organic synthesis. / Kochi, Takuya; Kanno, Shota; Kakiuchi, Fumitoshi.

In: Tetrahedron Letters, Vol. 60, No. 37, 150938, 12.09.2019.

Research output: Contribution to journalReview article

@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",
year = "2019",
month = "9",
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

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

VL - 60

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 37

M1 - 150938

ER -