Recent Advances in Catalytic Systems for the Mechanistically Complex Morita–Baylis–Hillman Reaction
Since its discovery in the late 1960s, the Morita–Baylis–Hillman (MBH) reaction has remained a powerful carbon–carbon σ-bond-forming transformation, producing small polyfunctionalized molecules. While commonly catalyzed by Lewis basic organic molecules such as tertiary amines and phosphines, several...
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| Published in | ACS catalysis Vol. 13; no. 6; pp. 3864 - 3895 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
American Chemical Society
17.03.2023
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| Subjects | |
| Online Access | Get full text |
| ISSN | 2155-5435 2155-5435 |
| DOI | 10.1021/acscatal.2c06420 |
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| Abstract | Since its discovery in the late 1960s, the Morita–Baylis–Hillman (MBH) reaction has remained a powerful carbon–carbon σ-bond-forming transformation, producing small polyfunctionalized molecules. While commonly catalyzed by Lewis basic organic molecules such as tertiary amines and phosphines, several advances in functional catalysts and reaction conditions have been made in order to improve the reaction rate, substrate scope, and enantioselectivity. The goal of this Review is to give an updated summary of the main improvements made in catalytic systems for the MBH reaction over the past decade until nowadays. We hope this account will instigate further investigations in order to circumvent the remaining challenges of this fascinating transformation. |
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| AbstractList | Since its discovery in the late 1960s, the Morita–Baylis–Hillman (MBH) reaction has remained a powerful carbon–carbon σ-bond-forming transformation, producing small polyfunctionalized molecules. While commonly catalyzed by Lewis basic organic molecules such as tertiary amines and phosphines, several advances in functional catalysts and reaction conditions have been made in order to improve the reaction rate, substrate scope, and enantioselectivity. The goal of this Review is to give an updated summary of the main improvements made in catalytic systems for the MBH reaction over the past decade until nowadays. We hope this account will instigate further investigations in order to circumvent the remaining challenges of this fascinating transformation. |
| Author | Almeida, Wanda P. Coelho, Fernando Fernandes, Fábio S. Santos, Hugo Rodrigues, Manoel T. Gomes, Ralph C. Zeoly, Lucas A. |
| AuthorAffiliation | Institute of Chemistry |
| AuthorAffiliation_xml | – name: Institute of Chemistry |
| Author_xml | – sequence: 1 givenname: Hugo orcidid: 0000-0002-7411-5180 surname: Santos fullname: Santos, Hugo – sequence: 2 givenname: Lucas A. orcidid: 0000-0003-2111-3904 surname: Zeoly fullname: Zeoly, Lucas A. – sequence: 3 givenname: Manoel T. orcidid: 0000-0001-9230-5642 surname: Rodrigues fullname: Rodrigues, Manoel T. – sequence: 4 givenname: Fábio S. surname: Fernandes fullname: Fernandes, Fábio S. – sequence: 5 givenname: Ralph C. surname: Gomes fullname: Gomes, Ralph C. – sequence: 6 givenname: Wanda P. surname: Almeida fullname: Almeida, Wanda P. – sequence: 7 givenname: Fernando orcidid: 0000-0003-1800-1549 surname: Coelho fullname: Coelho, Fernando email: facoelho@unicamp.br |
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| Keywords | Lewis acid organocatalysis enzyme multicatalysis Morita−Baylis−Hillman Lewis base enzymatic catalysis |
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