Rhodium (ii) carbene C-H insertion in water and catalyst reuse

Nuno R. Candeias; Pedro M. P. Gois; Carlos A. M. Afonso

doi:10.1590/S0100-40422007000700047

Rhodium (ii) carbene C-H insertion in water and catalyst reuse

Nuno R. Candeias, Pedro M. P. Gois, Carlos A. M. Afonso

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

2 Citations (Scopus)

Abstract

A five-session laboratory experiment is described for the synthesis of a P-lactam via Rh(II) catalysed intramolecular C-H insertion of a alpha-diazo-alpha-ethoxycarbonylacetamide. The metallo-carbene, responsible for the C-H bond activation, was generated from the diazo substrate and the catalyst Rh-2(OAc)(4). The high stability and solubility of the catalyst and the exclusive C-H insertion of the Rh-carbene allows the synthesis of this important heterocycle in water and the catalyst reutilization.

Original language	Undefined/Unknown
Pages (from-to)	1768-1772
Number of pages	5
Journal	Quimica Nova
Volume	30
Issue number	7
DOIs	https://doi.org/10.1590/S0100-40422007000700047
Publication status	Published - 2007
Externally published	Yes
Publication type	A1 Journal article-refereed

Keywords

dirhodium carbenoids
alpha-diazoacetamides
ORGANIC-SYNTHESIS
GREEN CHEMISTRY
ALPHA-DIAZOACETAMIDES
DIAZO-COMPOUNDS
ACTIVATION
TRANSFORMATIONS
DECOMPOSITION
STEREOCONTROL
SEPARATION
COMPOUND

Access to Document

10.1590/S0100-40422007000700047

Cite this

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title = "Rhodium (ii) carbene C-H insertion in water and catalyst reuse",

abstract = "A five-session laboratory experiment is described for the synthesis of a P-lactam via Rh(II) catalysed intramolecular C-H insertion of a alpha-diazo-alpha-ethoxycarbonylacetamide. The metallo-carbene, responsible for the C-H bond activation, was generated from the diazo substrate and the catalyst Rh-2(OAc)(4). The high stability and solubility of the catalyst and the exclusive C-H insertion of the Rh-carbene allows the synthesis of this important heterocycle in water and the catalyst reutilization.",

keywords = "dirhodium carbenoids, alpha-diazoacetamides, ORGANIC-SYNTHESIS, GREEN CHEMISTRY, ALPHA-DIAZOACETAMIDES, DIAZO-COMPOUNDS, ACTIVATION, TRANSFORMATIONS, DECOMPOSITION, STEREOCONTROL, SEPARATION, COMPOUND",

author = "Candeias, {Nuno R.} and Gois, {Pedro M. P.} and Afonso, {Carlos A. M.}",

year = "2007",

doi = "10.1590/S0100-40422007000700047",

language = "Ei tiedossa",

volume = "30",

pages = "1768--1772",

journal = "Quimica Nova",

issn = "0100-4042",

publisher = "Sociedade Brasileira de Quimica",

number = "7",

}

TY - JOUR

T1 - Rhodium (ii) carbene C-H insertion in water and catalyst reuse

AU - Candeias, Nuno R.

AU - Gois, Pedro M. P.

AU - Afonso, Carlos A. M.

PY - 2007

Y1 - 2007

N2 - A five-session laboratory experiment is described for the synthesis of a P-lactam via Rh(II) catalysed intramolecular C-H insertion of a alpha-diazo-alpha-ethoxycarbonylacetamide. The metallo-carbene, responsible for the C-H bond activation, was generated from the diazo substrate and the catalyst Rh-2(OAc)(4). The high stability and solubility of the catalyst and the exclusive C-H insertion of the Rh-carbene allows the synthesis of this important heterocycle in water and the catalyst reutilization.

AB - A five-session laboratory experiment is described for the synthesis of a P-lactam via Rh(II) catalysed intramolecular C-H insertion of a alpha-diazo-alpha-ethoxycarbonylacetamide. The metallo-carbene, responsible for the C-H bond activation, was generated from the diazo substrate and the catalyst Rh-2(OAc)(4). The high stability and solubility of the catalyst and the exclusive C-H insertion of the Rh-carbene allows the synthesis of this important heterocycle in water and the catalyst reutilization.

KW - dirhodium carbenoids

KW - alpha-diazoacetamides

KW - ORGANIC-SYNTHESIS

KW - GREEN CHEMISTRY

KW - ALPHA-DIAZOACETAMIDES

KW - DIAZO-COMPOUNDS

KW - ACTIVATION

KW - TRANSFORMATIONS

KW - DECOMPOSITION

KW - STEREOCONTROL

KW - SEPARATION

KW - COMPOUND

U2 - 10.1590/S0100-40422007000700047

DO - 10.1590/S0100-40422007000700047

M3 - Artikkeli

SN - 0100-4042

VL - 30

SP - 1768

EP - 1772

JO - Quimica Nova

JF - Quimica Nova

IS - 7

ER -