A highly efficient procedure for hydroformylation and hydroamino-vinylation of methyl acrylate

Matthew L. Clarke; Geoffrey J. Roff

doi:10.1039/b616918j

A highly efficient procedure for hydroformylation and hydroamino-vinylation of methyl acrylate

Matthew L. Clarke, Geoffrey J. Roff

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

38 Citations (Scopus)

Abstract

Methyl acrylate has been hydroformylated to the branched aldehyde with essentially perfect regio-selectivity and extraordinarily high average turnover frequencies ( up to 4000 h(-1)). Using 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane based Rh catalyst with a substrate to catalyst ratio of 10 000, hydroformylation in excellent yield was achieved with complete branched selectivity in around 2 h. Performing this reaction in the presence of aromatic amines gave very high yields of the corresponding enamines in a quick one pot domino hydroaminovinylation reaction. Remarkably, this latter reaction works best under solvent-free conditions.

Original language	English
Pages (from-to)	792-796
Number of pages	5
Journal	Green Chemistry
Volume	9
DOIs	https://doi.org/10.1039/b616918j
Publication status	Published - 2007

Keywords

CATALYZED ASYMMETRIC HYDROFORMYLATION
RHODIUM(I) COMPLEXES
ENANTIOSELECTIVE HYDROFORMYLATION
SUPERCRITICAL CO2
PHOSPHITE LIGANDS
OLEFINS
DERIVATIVES
CHEMISTRY
ESTERS

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title = "A highly efficient procedure for hydroformylation and hydroamino-vinylation of methyl acrylate",

abstract = "Methyl acrylate has been hydroformylated to the branched aldehyde with essentially perfect regio-selectivity and extraordinarily high average turnover frequencies ( up to 4000 h(-1)). Using 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane based Rh catalyst with a substrate to catalyst ratio of 10 000, hydroformylation in excellent yield was achieved with complete branched selectivity in around 2 h. Performing this reaction in the presence of aromatic amines gave very high yields of the corresponding enamines in a quick one pot domino hydroaminovinylation reaction. Remarkably, this latter reaction works best under solvent-free conditions.",

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year = "2007",

doi = "10.1039/b616918j",

language = "English",

volume = "9",

pages = "792--796",

journal = "Green Chemistry",

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publisher = "Royal Society of Chemistry",

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T1 - A highly efficient procedure for hydroformylation and hydroamino-vinylation of methyl acrylate

AU - Clarke, Matthew L.

AU - Roff, Geoffrey J.

PY - 2007

Y1 - 2007

N2 - Methyl acrylate has been hydroformylated to the branched aldehyde with essentially perfect regio-selectivity and extraordinarily high average turnover frequencies ( up to 4000 h(-1)). Using 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane based Rh catalyst with a substrate to catalyst ratio of 10 000, hydroformylation in excellent yield was achieved with complete branched selectivity in around 2 h. Performing this reaction in the presence of aromatic amines gave very high yields of the corresponding enamines in a quick one pot domino hydroaminovinylation reaction. Remarkably, this latter reaction works best under solvent-free conditions.

AB - Methyl acrylate has been hydroformylated to the branched aldehyde with essentially perfect regio-selectivity and extraordinarily high average turnover frequencies ( up to 4000 h(-1)). Using 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane based Rh catalyst with a substrate to catalyst ratio of 10 000, hydroformylation in excellent yield was achieved with complete branched selectivity in around 2 h. Performing this reaction in the presence of aromatic amines gave very high yields of the corresponding enamines in a quick one pot domino hydroaminovinylation reaction. Remarkably, this latter reaction works best under solvent-free conditions.

KW - CATALYZED ASYMMETRIC HYDROFORMYLATION

KW - RHODIUM(I) COMPLEXES

KW - ENANTIOSELECTIVE HYDROFORMYLATION

KW - SUPERCRITICAL CO2

KW - PHOSPHITE LIGANDS

KW - OLEFINS

KW - DERIVATIVES

KW - CHEMISTRY

KW - ESTERS

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U2 - 10.1039/b616918j

DO - 10.1039/b616918j

M3 - Article

SN - 1463-9262

VL - 9

SP - 792

EP - 796

JO - Green Chemistry

JF - Green Chemistry

ER -

A highly efficient procedure for hydroformylation and hydroamino-vinylation of methyl acrylate

Abstract

Keywords

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