Literature DB >> 30605319

Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

Cian Kingston1, Michael A Wallace2, Alban J Allentoff2, Justine N deGruyter1, Jason S Chen3, Sharon X Gong2, Samuel Bonacorsi2, Phil S Baran1.   

Abstract

A two-step degradation-reconstruction approach to the carbon-14 radiolabeling of alkyl carboxylic acids is presented. Simple activation via redox-active ester formation was followed by nickel-mediated decarboxylative carboxylation to afford a range of complex compounds with ample isotopic incorporations for drug metabolism and pharmacokinetic studies. The practicality and operational simplicity of the protocol were demonstrated by its use in an industrial carbon-14 radiolabeling setting.

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Year:  2019        PMID： 30605319      PMCID： PMC7000106          DOI： 10.1021/jacs.8b12035

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  51 in total

1.  Use of a microplate scintillation counter as a radioactivity detector for miniaturized separation techniques in drug metabolism.

Authors:  K O Boernsen; J M Floeckher; G J Bruin
Journal:  Anal Chem       Date:  2000-08-15       Impact factor: 6.986

Review 2.  Manufacturing of [(14)C]-Labeled Drug Substance and Drug Product Utilized in Clinical Research: A Case Study of Omecamtiv Mecarbil.

Authors:  Scott W Roberts; Jeroen M Bezemer; Michael T Kennedy; Tiffany L Correll; Raju Subramanian; Shawn D Walker
Journal:  Curr Pharm Des       Date:  2016       Impact factor: 3.116

3.  A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents.

Authors:  Tian Qin; Josep Cornella; Chao Li; Lara R Malins; Jacob T Edwards; Shuhei Kawamura; Brad D Maxwell; Martin D Eastgate; Phil S Baran
Journal:  Science       Date:  2016-04-21       Impact factor: 47.728

Review 4.  Quantitative whole-body autoradiography: past, present and future.

Authors:  Andrew McEwen; Claire Henson
Journal:  Bioanalysis       Date:  2015       Impact factor: 2.681

5.  Biotransformation of [14C]-ixazomib in patients with advanced solid tumors: characterization of metabolite profiles in plasma, urine, and feces.

Authors:  Sandeepraj Pusalkar; Mihaela Plesescu; Neeraj Gupta; Michael Hanley; Karthik Venkatakrishnan; Jing-Tao Wu; Cindy Xia; Xiaoquan Zhang; Swapan Chowdhury
Journal:  Cancer Chemother Pharmacol       Date:  2018-08-20       Impact factor: 3.333

6.  Fragment Coupling with Tertiary Radicals Generated by Visible-Light Photocatalysis.

Authors:  Christopher R Jamison; Larry E Overman
Journal:  Acc Chem Res       Date:  2016-08-04       Impact factor: 22.384

7.  Development of Decarboxylative Cyanation Reactions for C-13/C-14 Carboxylic Acid Labeling Using an Electrophilic Cyanating Reagent.

Authors:  Fengbin Song; Rhys Salter; Lu Chen
Journal:  J Org Chem       Date:  2017-03-16       Impact factor: 4.354

Review 8.  Carboxylic acids as substrates in homogeneous catalysis.

Authors:  Lukas J Goossen; Nuria Rodríguez; Käthe Goossen
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Iron-catalysed tritiation of pharmaceuticals.

Authors:  Renyuan Pony Yu; David Hesk; Nelo Rivera; István Pelczer; Paul J Chirik
Journal:  Nature       Date:  2016-01-14       Impact factor: 49.962

10.  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
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  9 in total

1.  A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

Authors:  Shengyang Ni; Natalia M Padial; Cian Kingston; Julien C Vantourout; Daniel C Schmitt; Jacob T Edwards; Monika M Kruszyk; Rohan R Merchant; Pavel K Mykhailiuk; Brittany B Sanchez; Shouliang Yang; Matthew A Perry; Gary M Gallego; James J Mousseau; Michael R Collins; Robert J Cherney; Pavlo S Lebed; Jason S Chen; Tian Qin; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-04-16       Impact factor: 15.419

2.  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

3.  Development of an Improved System for the Carboxylation of Aryl Halides through Mechanistic Studies.

Authors:  David J Charboneau; Gary W Brudvig; Nilay Hazari; Hannah M C Lant; Andrew K Saydjari
Journal:  ACS Catal       Date:  2019-03-14       Impact factor: 13.084

4.  Convergent Synthesis of (R)-Silodosin via Decarboxylative Cross-Coupling.

Authors:  Tie-Gen Chen; Lucas Mele; Olivier Jentzer; Dominique Delbrayelle; Pierre-Georges Echeverria; Julien C Vantourout; Phil S Baran
Journal:  Tetrahedron Lett       Date:  2021-07-24       Impact factor: 2.032

Review 5.  The Emergence of Carbon Isotope Exchange.

Authors:  Karen Hinsinger; Grégory Pieters
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-12       Impact factor: 15.336

Review 6.  Late-Stage Carbon-14 Labeling and Isotope Exchange: Emerging Opportunities and Future Challenges.

Authors:  Victor Babin; Frédéric Taran; Davide Audisio
Journal:  JACS Au       Date:  2022-06-07

7.  1,2-Difunctionalized bicyclo[1.1.1]pentanes: Long-sought-after mimetics for ortho/meta-substituted arenes.

Authors:  Jin-Xin Zhao; Yu-Xuan Chang; Chi He; Benjamin J Burke; Michael R Collins; Matthew Del Bel; Jeff Elleraas; Gary M Gallego; T Patrick Montgomery; James J Mousseau; Sajiv K Nair; Matthew A Perry; Jillian E Spangler; Julien C Vantourout; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2021-07-13       Impact factor: 11.205

8.  Carbon-11 carboxylation of trialkoxysilane and trimethylsilane derivatives using [11C]CO2.

Authors:  Salvatore Bongarzone; Nicola Raucci; Igor Camargo Fontana; Federico Luzi; Antony D Gee
Journal:  Chem Commun (Camb)       Date:  2020-03-25       Impact factor: 6.222

Review 9.  Radical-Based Synthesis and Modification of Amino Acids.

Authors:  Francisco José Aguilar Troyano; Kay Merkens; Khadijah Anwar; Adrián Gómez-Suárez
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-04       Impact factor: 15.336
  9 in total

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