Literature DB >> 26526115

Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms.

Simon B Lang1, Kathryn M O'Nele1, Justin T Douglas1, Jon A Tunge2.   

Abstract

The room temperature radical decarboxylative allylation of N-protected α-amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α-amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylation; amino acids; cross-coupling; homogeneous catalysis; photocatalysis

Mesh：

Substances：

Year:  2015        PMID： 26526115      PMCID： PMC4715668          DOI： 10.1002/chem.201503644

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  32 in total

1.  Catalytic enantioselective allylation of carbonyl compounds and imines.

Authors:  Miguel Yus; José C González-Gómez; Francisco Foubelo
Journal:  Chem Rev       Date:  2011-09-16       Impact factor: 60.622

2.  Combining gold and photoredox catalysis: visible light-mediated oxy- and aminoarylation of alkenes.

Authors:  Basudev Sahoo; Matthew N Hopkinson; Frank Glorius
Journal:  J Am Chem Soc       Date:  2013-04-08       Impact factor: 15.419

3.  Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives.

Authors:  Erin C Burger; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2006-08-09       Impact factor: 15.419

4.  Quantum-chemical predictions of absolute standard redox potentials of diverse organic molecules and free radicals in acetonitrile.

Authors:  Yao Fu; Lei Liu; Hai-Zhu Yu; Yi-Min Wang; Qing-Xiang Guo
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

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.  Photo-activation of Pd-catalyzed Sonogashira coupling using a Ru/bipyridine complex as energy transfer agent.

Authors:  Masahisa Osawa; Hidetada Nagai; Munetaka Akita
Journal:  Dalton Trans       Date:  2007-01-15       Impact factor: 4.390

7.  Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling.

Authors:  David N Primer; Idris Karakaya; John C Tellis; Gary A Molander
Journal:  J Am Chem Soc       Date:  2015-02-04       Impact factor: 15.419

8.  Tin-free radical chemistry using the persistent radical effect: alkoxyamine isomerization, addition reactions and polymerizations.

Authors:  Armido Studer
Journal:  Chem Soc Rev       Date:  2004-05-18       Impact factor: 54.564

9.  C-C bond-forming reactions via Pd-mediated decarboxylative alpha-imino anion generation.

Authors:  Andrew A Yeagley; Jason J Chruma
Journal:  Org Lett       Date:  2007-06-20       Impact factor: 6.005

10.  Decarboxylative arylation of α-amino acids via photoredox catalysis: a one-step conversion of biomass to drug pharmacophore.

Authors:  Zhiwei Zuo; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2014-03-31       Impact factor: 15.419
View more
  10 in total

1.  Preparation of visible-light-activated metal complexes and their use in photoredox/nickel dual catalysis.

Authors:  Christopher B Kelly; Niki R Patel; David N Primer; Matthieu Jouffroy; John C Tellis; Gary A Molander
Journal:  Nat Protoc       Date:  2017-02-02       Impact factor: 13.491

2.  Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond.

Authors:  Kelvin Pak Shing Cheung; Daria Kurandina; Tetsuji Yata; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2020-05-19       Impact factor: 15.419

3.  Photocatalytic Aminodecarboxylation of Carboxylic Acids.

Authors:  Simon B Lang; Kaitie C Cartwright; Richard S Welter; Theresa M Locascio; Jon A Tunge
Journal:  European J Org Chem       Date:  2016-06-19

4.  Photoredox Catalysis in Organic Chemistry.

Authors:  Megan H Shaw; Jack Twilton; David W C MacMillan
Journal:  J Org Chem       Date:  2016-08-01       Impact factor: 4.354

Review 5.  Dual Catalysis Strategies in Photochemical Synthesis.

Authors:  Kazimer L Skubi; Travis R Blum; Tehshik P Yoon
Journal:  Chem Rev       Date:  2016-04-25       Impact factor: 60.622

6.  Visible light-promoted CO2 fixation with imines to synthesize diaryl α-amino acids.

Authors:  Xinyuan Fan; Xu Gong; Mengyue Ma; Rui Wang; Patrick J Walsh
Journal:  Nat Commun       Date:  2018-11-22       Impact factor: 14.919

7.  Regio-, Diastereo-, and Enantioselective Decarboxylative Hydroaminoalkylation of Dienol Ethers Enabled by Dual Palladium/Photoredox Catalysis.

Authors:  Jun Zheng; Nana Tang; Hui Xie; Bernhard Breit
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-16       Impact factor: 16.823

8.  Organophotoredox/palladium dual catalytic decarboxylative Csp3-Csp3 coupling of carboxylic acids and π-electrophiles.

Authors:  Kaitie C Cartwright; Jon A Tunge
Journal:  Chem Sci       Date:  2020-07-16       Impact factor: 9.825

Review 9.  Photoredox Catalysis Unlocks Single-Electron Elementary Steps in Transition Metal Catalyzed Cross-Coupling.

Authors:  Mark D Levin; Suhong Kim; F Dean Toste
Journal:  ACS Cent Sci       Date:  2016-05-03       Impact factor: 14.553

10.  Visible Light Photoredox Cross-Coupling of Acyl Chlorides with Potassium Alkoxymethyltrifluoroborates: Synthesis of α-Alkoxyketones.

Authors:  Javad Amani; Esmat Sodagar; Gary A Molander
Journal:  Org Lett       Date:  2016-02-01       Impact factor: 6.005
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.