Well-defined [Rh(NHC)(OH)] complexes enabling the conjugate addition of arylboronic acids to α, β-unsaturated ketones

Byron J. Truscott; George C. Fortman; Alexandra M. Z. Slawin; Steven P. Nolan

doi:10.1039/C1OB06112G

Well-defined [Rh(NHC)(OH)] complexes enabling the conjugate addition of arylboronic acids to α, β-unsaturated ketones

Byron J. Truscott, George C. Fortman, Alexandra M. Z. Slawin, Steven P. Nolan

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

37 Citations (Scopus)

Abstract

The synthesis and catalytic activity of three well-defined monomeric rhodium(I) hydroxide complexes bearing N-heterocyclic carbene (NHC) ligands are reported. [Rh(cod)(ICy)(OH)] promoted the 1,4-addition of arylboronic acids to cyclic enones, with TONs and TOFs of 100,000 and 6,600 h-1, respectively, at 0.001 mol% catalyst loadings. Mechanistic studies permitted the isolation of a phenylrhodium intermediate.

Original language	English
Pages (from-to)	7038-7041
Number of pages	4
Journal	Organic & Biomolecular Chemistry
Volume	9
Issue number	20
Early online date	22 Aug 2011
DOIs	https://doi.org/10.1039/C1OB06112G
Publication status	Published - 2011

Keywords

CATALYZED ASYMMETRIC 1,4-ADDITION
CROSS-COUPLING REACTION
CHIRAL DIENE LIGANDS
CARBONYL-COMPOUNDS
7,7'-DISUBSTITUTED BINAPS
PHENYLBORONIC ACID
ROOM-TEMPERATURE
RHODIUM CATALYST
HIGH-PERFORMANCE
ENONES

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@article{184d3189e55048ad910971a490ab36a8,

title = "Well-defined [Rh(NHC)(OH)] complexes enabling the conjugate addition of arylboronic acids to α, β-unsaturated ketones",

abstract = "The synthesis and catalytic activity of three well-defined monomeric rhodium(I) hydroxide complexes bearing N-heterocyclic carbene (NHC) ligands are reported. [Rh(cod)(ICy)(OH)] promoted the 1,4-addition of arylboronic acids to cyclic enones, with TONs and TOFs of 100,000 and 6,600 h-1, respectively, at 0.001 mol% catalyst loadings. Mechanistic studies permitted the isolation of a phenylrhodium intermediate.",

keywords = "CATALYZED ASYMMETRIC 1,4-ADDITION, CROSS-COUPLING REACTION, CHIRAL DIENE LIGANDS, CARBONYL-COMPOUNDS, 7,7'-DISUBSTITUTED BINAPS, PHENYLBORONIC ACID, ROOM-TEMPERATURE, RHODIUM CATALYST, HIGH-PERFORMANCE, ENONES",

author = "Truscott, {Byron J.} and Fortman, {George C.} and Slawin, {Alexandra M. Z.} and Nolan, {Steven P.}",

year = "2011",

doi = "10.1039/C1OB06112G",

language = "English",

volume = "9",

pages = "7038--7041",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "20",

}

TY - JOUR

T1 - Well-defined [Rh(NHC)(OH)] complexes enabling the conjugate addition of arylboronic acids to α, β-unsaturated ketones

AU - Truscott, Byron J.

AU - Fortman, George C.

AU - Slawin, Alexandra M. Z.

AU - Nolan, Steven P.

PY - 2011

Y1 - 2011

N2 - The synthesis and catalytic activity of three well-defined monomeric rhodium(I) hydroxide complexes bearing N-heterocyclic carbene (NHC) ligands are reported. [Rh(cod)(ICy)(OH)] promoted the 1,4-addition of arylboronic acids to cyclic enones, with TONs and TOFs of 100,000 and 6,600 h-1, respectively, at 0.001 mol% catalyst loadings. Mechanistic studies permitted the isolation of a phenylrhodium intermediate.

AB - The synthesis and catalytic activity of three well-defined monomeric rhodium(I) hydroxide complexes bearing N-heterocyclic carbene (NHC) ligands are reported. [Rh(cod)(ICy)(OH)] promoted the 1,4-addition of arylboronic acids to cyclic enones, with TONs and TOFs of 100,000 and 6,600 h-1, respectively, at 0.001 mol% catalyst loadings. Mechanistic studies permitted the isolation of a phenylrhodium intermediate.

KW - CATALYZED ASYMMETRIC 1,4-ADDITION

KW - CROSS-COUPLING REACTION

KW - CHIRAL DIENE LIGANDS

KW - CARBONYL-COMPOUNDS

KW - 7,7'-DISUBSTITUTED BINAPS

KW - PHENYLBORONIC ACID

KW - ROOM-TEMPERATURE

KW - RHODIUM CATALYST

KW - HIGH-PERFORMANCE

KW - ENONES

U2 - 10.1039/C1OB06112G

DO - 10.1039/C1OB06112G

M3 - Article

SN - 1477-0520

VL - 9

SP - 7038

EP - 7041

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 20

ER -

Well-defined [Rh(NHC)(OH)] complexes enabling the conjugate addition of arylboronic acids to α, β-unsaturated ketones

Abstract

Keywords

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