Literature DB >> 36105339

Decarboxylative Cross-Coupling: A Radical Tool in Medicinal Chemistry.

Gabriele Laudadio1, Maximilian D Palkowitz1, Tamara El-Hayek Ewing1, Phil S Baran1.   

Abstract

Carboxylic acids, the most versatile and ubiquitous diversity input used in medicinal chemistry for canonical polar bond constructions such as amide synthesis, can now be employed in a fundamentally different category of reaction to make C-C bonds by harnessing the power of radicals. This outlook serves as a user-guide to aid practitioners in both the design of syntheses that leverage the simplifying power of this disconnection and the precise tactics that can be employed to enable them. Taken together, this emerging area holds the potential to rapidly accelerate access to chemical space of value to modern medicinal chemistry.
© 2022 American Chemical Society.

Entities:  

Year:  2022        PMID: 36105339      PMCID: PMC9465705          DOI: 10.1021/acsmedchemlett.2c00286

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN: 1948-5875            Impact factor:   4.632


  43 in total

1.  The Ireland-Claisen rearrangement strategy towards the synthesis of the schizophrenia drug, (+)-asenapine.

Authors:  Raghunath Reddy Anugu; Prathama S Mainkar; Balasubramanian Sridhar; Srivari Chandrasekhar
Journal:  Org Biomol Chem       Date:  2015-12-11       Impact factor: 3.876

Review 2.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

Review 3.  New and unusual scaffolds in medicinal chemistry.

Authors:  Charles M Marson
Journal:  Chem Soc Rev       Date:  2011-08-12       Impact factor: 54.564

4.  Electrochemical Decarboxylative N-Alkylation of Heterocycles.

Authors:  Tao Sheng; Hai-Jun Zhang; Ming Shang; Chi He; Julien C Vantourout; Phil S Baran
Journal:  Org Lett       Date:  2020-09-17       Impact factor: 6.005

5.  Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Authors:  Zhiwei Zuo; Derek T Ahneman; Lingling Chu; Jack A Terrett; Abigail G Doyle; David W C MacMillan
Journal:  Science       Date:  2014-06-05       Impact factor: 47.728

6.  Decarboxylative coupling reactions: a modern strategy for C-C-bond formation.

Authors:  Nuria Rodríguez; Lukas J Goossen
Journal:  Chem Soc Rev       Date:  2011-07-27       Impact factor: 54.564

7.  Ni-electrocatalytic Csp3-Csp3 doubly decarboxylative coupling.

Authors:  Benxiang Zhang; Yang Gao; Yuta Hioki; Martins S Oderinde; Jennifer X Qiao; Kevin X Rodriguez; Hai-Jun Zhang; Yu Kawamata; Phil S Baran
Journal:  Nature       Date:  2022-04-05       Impact factor: 69.504

8.  Merging photoredox and nickel catalysis: decarboxylative cross-coupling of carboxylic acids with vinyl halides.

Authors:  Adam Noble; Stefan J McCarver; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2015-01-12       Impact factor: 15.419

9.  Decarboxylative alkenylation.

Authors:  Jacob T Edwards; Rohan R Merchant; Kyle S McClymont; Kyle W Knouse; Tian Qin; Lara R Malins; Benjamin Vokits; Scott A Shaw; Deng-Hui Bao; Fu-Liang Wei; Ting Zhou; Martin D Eastgate; Phil S Baran
Journal:  Nature       Date:  2017-04-19       Impact factor: 49.962

Review 10.  Impact of Cross-Coupling Reactions in Drug Discovery and Development.

Authors:  Melissa J Buskes; Maria-Jesus Blanco
Journal:  Molecules       Date:  2020-07-31       Impact factor: 4.411

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