Intermolecular hydroacylation by transition-metal complexes

Chul-Ho Jun, Eun Ae Jo, Jung Woo Park

Research output: Contribution to journalShort survey

162 Citations (Scopus)

Abstract

In this review, transition-metal-catalyzed intermolecular hydroacylation, which is a direct synthetic protocol generating ketones from aldehydes and unsaturated hydrocarbons, will be discussed. In order to avoid decarbonylation, one of the major side-reactions occurring in transition-metal-catalyzed hydroacylation, several important strategies have been developed: An aldehyde ligand bearing a coordinating heteroatom at an appropriate position, a chelation auxiliary, and a masked form of the aldehyde, such as an aldimine or allylamine. Hydroacylation or its variations can also be applied to the synthesis of cycloalkanones and an α,β-unsaturated ketone or to the carbon-carbon triple bond cleavage of an alkyne.

Original languageEnglish
Pages (from-to)1869-1881
Number of pages13
JournalEuropean Journal of Organic Chemistry
Issue number12
DOIs
Publication statusPublished - 2007 Jun 22

Fingerprint

Coordination Complexes
aldehydes
Aldehydes
Transition metals
transition metals
Ketones
ketones
Bearings (structural)
Carbon
Allylamine
chelation
Alkynes
carbon
alkynes
Hydrocarbons
Chelation
cleavage
hydrocarbons
Ligands
ligands

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

@article{043efd55be4f4d4da018630fc51be46f,
title = "Intermolecular hydroacylation by transition-metal complexes",
abstract = "In this review, transition-metal-catalyzed intermolecular hydroacylation, which is a direct synthetic protocol generating ketones from aldehydes and unsaturated hydrocarbons, will be discussed. In order to avoid decarbonylation, one of the major side-reactions occurring in transition-metal-catalyzed hydroacylation, several important strategies have been developed: An aldehyde ligand bearing a coordinating heteroatom at an appropriate position, a chelation auxiliary, and a masked form of the aldehyde, such as an aldimine or allylamine. Hydroacylation or its variations can also be applied to the synthesis of cycloalkanones and an α,β-unsaturated ketone or to the carbon-carbon triple bond cleavage of an alkyne.",
author = "Chul-Ho Jun and Jo, {Eun Ae} and Park, {Jung Woo}",
year = "2007",
month = "6",
day = "22",
doi = "10.1002/ejoc.200600846",
language = "English",
pages = "1869--1881",
journal = "Annalen der Pharmacie",
issn = "0075-4617",
publisher = "Wiley-VCH Verlag",
number = "12",

}

Intermolecular hydroacylation by transition-metal complexes. / Jun, Chul-Ho; Jo, Eun Ae; Park, Jung Woo.

In: European Journal of Organic Chemistry, No. 12, 22.06.2007, p. 1869-1881.

Research output: Contribution to journalShort survey

TY - JOUR

T1 - Intermolecular hydroacylation by transition-metal complexes

AU - Jun, Chul-Ho

AU - Jo, Eun Ae

AU - Park, Jung Woo

PY - 2007/6/22

Y1 - 2007/6/22

N2 - In this review, transition-metal-catalyzed intermolecular hydroacylation, which is a direct synthetic protocol generating ketones from aldehydes and unsaturated hydrocarbons, will be discussed. In order to avoid decarbonylation, one of the major side-reactions occurring in transition-metal-catalyzed hydroacylation, several important strategies have been developed: An aldehyde ligand bearing a coordinating heteroatom at an appropriate position, a chelation auxiliary, and a masked form of the aldehyde, such as an aldimine or allylamine. Hydroacylation or its variations can also be applied to the synthesis of cycloalkanones and an α,β-unsaturated ketone or to the carbon-carbon triple bond cleavage of an alkyne.

AB - In this review, transition-metal-catalyzed intermolecular hydroacylation, which is a direct synthetic protocol generating ketones from aldehydes and unsaturated hydrocarbons, will be discussed. In order to avoid decarbonylation, one of the major side-reactions occurring in transition-metal-catalyzed hydroacylation, several important strategies have been developed: An aldehyde ligand bearing a coordinating heteroatom at an appropriate position, a chelation auxiliary, and a masked form of the aldehyde, such as an aldimine or allylamine. Hydroacylation or its variations can also be applied to the synthesis of cycloalkanones and an α,β-unsaturated ketone or to the carbon-carbon triple bond cleavage of an alkyne.

UR - http://www.scopus.com/inward/record.url?scp=34250618375&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34250618375&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200600846

DO - 10.1002/ejoc.200600846

M3 - Short survey

SP - 1869

EP - 1881

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

IS - 12

ER -