Borrowing hydrogen: iridium-catalyzed reactions for the formation of C-C bonds from alcohols

Phillip J Black; Gerta Cami-Kobeci; Michael G Edwards; Paul A Slatford; Michael K Whittlesey; Jonathan M J Williams

Borrowing hydrogen: iridium-catalyzed reactions for the formation of C-C bonds from alcohols

Phillip J Black
, Gerta Cami-Kobeci
, Michael G Edwards
, Paul A Slatford
, Michael K Whittlesey
, Jonathan M J Williams

Department of Chemistry

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

98 Citations (SciVal)

Abstract

Alcs. have been employed as substrates for C-C bond-forming reactions which involve initial activation by the temporary removal of hydrogen to form an aldehyde. The intermediate aldehyde is converted into an alkene via a Horner-Wadsworth-Emmons reaction, nitroaldol and aldol reactions. The borrowed hydrogen is then returned to the alkene to form a C-C bond.

Original language	English
Pages (from-to)	116-125
Number of pages	10
Journal	Organic and Biomolecular Chemistry
Volume	4
Issue number	1
Publication status	Published - 2006

Keywords

Addition reaction
Ketones Role
RACT (Reactant or reagent) (iridium-catalyzed reactions for formation of C-C bonds from alcs. via intermediate conversion to aldehyde)
Addition reaction catalysts
RACT (Reactant or reagent) (nitro
RCT (Reactant)
Aldol condensation
Horner Wadsworth Emmons reaction
alc addn nitroalkane phosphonate ketone iridium catalyst
Alcohols
Aldol condensation catalysts
iridium-catalyzed reactions for formation of C-C bonds from alcs. via intermediate conversion to aldehyde)
Alkanes Role
Horner Wadsworth Emmons reaction catalysts (iridium-catalyzed reactions for formation of C-C bonds from alcs. via intermediate conversion to aldehyde)

Cite this

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title = "Borrowing hydrogen: iridium-catalyzed reactions for the formation of C-C bonds from alcohols",

abstract = "Alcs. have been employed as substrates for C-C bond-forming reactions which involve initial activation by the temporary removal of hydrogen to form an aldehyde. The intermediate aldehyde is converted into an alkene via a Horner-Wadsworth-Emmons reaction, nitroaldol and aldol reactions. The borrowed hydrogen is then returned to the alkene to form a C-C bond.",

keywords = "Addition reaction, Ketones Role, RACT (Reactant or reagent) (iridium-catalyzed reactions for formation of C-C bonds from alcs. via intermediate conversion to aldehyde), Addition reaction catalysts, RACT (Reactant or reagent) (nitro, RCT (Reactant), Aldol condensation, Horner Wadsworth Emmons reaction, alc addn nitroalkane phosphonate ketone iridium catalyst, Alcohols, Aldol condensation catalysts, iridium-catalyzed reactions for formation of C-C bonds from alcs. via intermediate conversion to aldehyde), Alkanes Role, Horner Wadsworth Emmons reaction catalysts (iridium-catalyzed reactions for formation of C-C bonds from alcs. via intermediate conversion to aldehyde)",

author = "Black, \{Phillip J\} and Gerta Cami-Kobeci and Edwards, \{Michael G\} and Slatford, \{Paul A\} and Whittlesey, \{Michael K\} and Williams, \{Jonathan M J\}",

year = "2006",

language = "English",

volume = "4",

pages = "116--125",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "1",

}

TY - JOUR

T1 - Borrowing hydrogen: iridium-catalyzed reactions for the formation of C-C bonds from alcohols

AU - Black, Phillip J

AU - Cami-Kobeci, Gerta

AU - Edwards, Michael G

AU - Slatford, Paul A

AU - Whittlesey, Michael K

AU - Williams, Jonathan M J

PY - 2006

Y1 - 2006

N2 - Alcs. have been employed as substrates for C-C bond-forming reactions which involve initial activation by the temporary removal of hydrogen to form an aldehyde. The intermediate aldehyde is converted into an alkene via a Horner-Wadsworth-Emmons reaction, nitroaldol and aldol reactions. The borrowed hydrogen is then returned to the alkene to form a C-C bond.

AB - Alcs. have been employed as substrates for C-C bond-forming reactions which involve initial activation by the temporary removal of hydrogen to form an aldehyde. The intermediate aldehyde is converted into an alkene via a Horner-Wadsworth-Emmons reaction, nitroaldol and aldol reactions. The borrowed hydrogen is then returned to the alkene to form a C-C bond.

KW - Addition reaction

KW - Ketones Role

KW - RACT (Reactant or reagent) (iridium-catalyzed reactions for formation of C-C bonds from alcs. via intermediate conversion to aldehyde)

KW - Addition reaction catalysts

KW - RACT (Reactant or reagent) (nitro

KW - RCT (Reactant)

KW - Aldol condensation

KW - Horner Wadsworth Emmons reaction

KW - alc addn nitroalkane phosphonate ketone iridium catalyst

KW - Alcohols

KW - Aldol condensation catalysts

KW - iridium-catalyzed reactions for formation of C-C bonds from alcs. via intermediate conversion to aldehyde)

KW - Alkanes Role

KW - Horner Wadsworth Emmons reaction catalysts (iridium-catalyzed reactions for formation of C-C bonds from alcs. via intermediate conversion to aldehyde)

M3 - Article

SN - 1477-0520

VL - 4

SP - 116

EP - 125

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 1

ER -

Borrowing hydrogen: iridium-catalyzed reactions for the formation of C-C bonds from alcohols

Abstract

Keywords

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