Intramolecular C-H insertion catalyzed by dirhodium(II) complexes using CO 2 as the reaction media

Małgorzata E. Zakrzewska; Pedro M.S.D. Cal; Nuno R. Candeias; Rafał Bogel-Łukasik; Carlos 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 CO ₂ as the reaction media

Małgorzata E. Zakrzewska, Pedro M.S.D. Cal, Nuno R. Candeias, Rafał Bogel-Łukasik, Carlos M. Afonso, Manuel N. Ponte, Pedro M.P. Gois

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

15 Citations (Scopus)

Abstract

In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO ₂ as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the β-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.

Original language	English
Pages (from-to)	211-240
Number of pages	30
Journal	Green Chemistry Letters and Reviews
Volume	5
Issue number	2
DOIs	https://doi.org/10.1080/17518253.2011.620009
Publication status	Published - Jun 2012

Keywords

C-H insertion.
diazoacetamides.
dirhodium(II).
lactams.
scCO

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10.1080/17518253.2011.620009

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title = "Intramolecular C-H insertion catalyzed by dirhodium(II) complexes using CO 2 as the reaction media",

abstract = "In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO 2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the β-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 = "C-H insertion., diazoacetamides., dirhodium(II)., lactams., scCO",

author = "Zakrzewska, {Ma{\l}gorzata E.} and Cal, {Pedro M.S.D.} and Candeias, {Nuno R.} and Rafa{\l} Bogel-{\L}ukasik and Afonso, {Carlos M.} and Ponte, {Manuel N.} and Gois, {Pedro M.P.}",

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month = jun,

doi = "10.1080/17518253.2011.620009",

language = "English",

volume = "5",

pages = "211--240",

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T1 - Intramolecular C-H insertion catalyzed by dirhodium(II) complexes using CO 2 as the reaction media

AU - Zakrzewska, Małgorzata E.

AU - Cal, Pedro M.S.D.

AU - Candeias, Nuno R.

AU - Bogel-Łukasik, Rafał

AU - Afonso, Carlos M.

AU - Ponte, Manuel N.

AU - Gois, Pedro M.P.

PY - 2012/6

Y1 - 2012/6

N2 - In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO 2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the β-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 CO 2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the β-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 - C-H insertion.

KW - diazoacetamides.

KW - dirhodium(II).

KW - lactams.

KW - scCO

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U2 - 10.1080/17518253.2011.620009

DO - 10.1080/17518253.2011.620009

M3 - Article

AN - SCOPUS:84859505886

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 CO ₂ as the reaction media

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Keywords

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