Intramolecular C-H insertion catalyzed by dirhodium(II) complexes using CO2 as the reaction media

Malgorzata E. Zakrzewska; Pedro M. S. D. Cal; Nuno R. Candeias; Rafal Bogel-Lukasik; Carlos A. M. Afonso; Manuel N. Ponte; Pedro M. P. Gois

doi:10.1080/17518253.2011.620009

Intramolecular C-H insertion catalyzed by dirhodium(II) complexes using CO2 as the reaction media

Malgorzata E. Zakrzewska, Pedro M. S. D. Cal, Nuno R. Candeias, Rafal Bogel-Lukasik, Carlos A. M. Afonso, Manuel N. Ponte, Pedro M. P. Gois

Tutkimustuotos: Artikkeli › Tieteellinen › vertaisarvioitu

15 Sitaatiot (Scopus)

Abstrakti

In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the beta-lactam 14 was obtained in > 97% yield and 65% ee using the chiral dirhodium(II) catalyst Rh-2(S-PTTL)(4). Finally, the dirhodium(II) complex Rh-2(OAc)(4) was used in two consecutive cycles in which complete conversion to the lactam was observed.

Alkuperäiskieli	Englanti
Sivut	211-240
Sivumäärä	30
Julkaisu	Green Chemistry Letters and Reviews
Vuosikerta	5
Numero	2
DOI - pysyväislinkit	https://doi.org/10.1080/17518253.2011.620009
Tila	Julkaistu - 2012
OKM-julkaisutyyppi	A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Pääsy asiakirjaan

10.1080/17518253.2011.620009

Siteeraa tätä

@article{696b91bbe2f045aebce68fc579d860fc,

title = "Intramolecular C-H insertion catalyzed by dirhodium(II) complexes using CO2 as the reaction media",

abstract = "In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the beta-lactam 14 was obtained in > 97% yield and 65% ee using the chiral dirhodium(II) catalyst Rh-2(S-PTTL)(4). Finally, the dirhodium(II) complex Rh-2(OAc)(4) was used in two consecutive cycles in which complete conversion to the lactam was observed.",

keywords = "diazoacetamides, C-H insertion, dirhodium(II), lactams, scCO(2), ASYMMETRIC CYCLOPROPANATION, ALPHA-DIAZOACETAMIDES, HOMOGENEOUS CATALYSIS, SUPERCRITICAL FLUIDS, CARBOXYLATES, ENANTIOSELECTIVITY, TRANSFORMATIONS, IMMOBILIZATION, ACTIVATION, STRATEGY",

author = "Zakrzewska, {Malgorzata E.} and Cal, {Pedro M. S. D.} and Candeias, {Nuno R.} and Rafal Bogel-Lukasik and Afonso, {Carlos A. M.} and Ponte, {Manuel N.} and Gois, {Pedro M. P.}",

year = "2012",

doi = "10.1080/17518253.2011.620009",

language = "English",

volume = "5",

pages = "211--240",

journal = "Green Chemistry Letters and Reviews",

issn = "1751-8253",

publisher = "Taylor and Francis Ltd.",

number = "2",

}

TY - JOUR

T1 - Intramolecular C-H insertion catalyzed by dirhodium(II) complexes using CO2 as the reaction media

AU - Zakrzewska, Malgorzata E.

AU - Cal, Pedro M. S. D.

AU - Candeias, Nuno R.

AU - Bogel-Lukasik, Rafal

AU - Afonso, Carlos A. M.

AU - Ponte, Manuel N.

AU - Gois, Pedro M. P.

PY - 2012

Y1 - 2012

N2 - In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the beta-lactam 14 was obtained in > 97% yield and 65% ee using the chiral dirhodium(II) catalyst Rh-2(S-PTTL)(4). Finally, the dirhodium(II) complex Rh-2(OAc)(4) was used in two consecutive cycles in which complete conversion to the lactam was observed.

AB - In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the beta-lactam 14 was obtained in > 97% yield and 65% ee using the chiral dirhodium(II) catalyst Rh-2(S-PTTL)(4). Finally, the dirhodium(II) complex Rh-2(OAc)(4) was used in two consecutive cycles in which complete conversion to the lactam was observed.

KW - diazoacetamides

KW - C-H insertion

KW - dirhodium(II)

KW - lactams

KW - scCO(2)

KW - ASYMMETRIC CYCLOPROPANATION

KW - ALPHA-DIAZOACETAMIDES

KW - HOMOGENEOUS CATALYSIS

KW - SUPERCRITICAL FLUIDS

KW - CARBOXYLATES

KW - ENANTIOSELECTIVITY

KW - TRANSFORMATIONS

KW - IMMOBILIZATION

KW - ACTIVATION

KW - STRATEGY

U2 - 10.1080/17518253.2011.620009

DO - 10.1080/17518253.2011.620009

M3 - Article

SN - 1751-8253

VL - 5

SP - 211

EP - 240

JO - Green Chemistry Letters and Reviews

JF - Green Chemistry Letters and Reviews

IS - 2

ER -

Intramolecular C-H insertion catalyzed by dirhodium(II) complexes using CO2 as the reaction media

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