Literature DB >> 28636185

Decarboxylative Alkynylation.

Joel M Smith1, Tian Qin1, Rohan R Merchant1, Jacob T Edwards1, Lara R Malins1, Zhiqing Liu2, Guanda Che2, Zichao Shen2, Scott A Shaw3, Martin D Eastgate4, Phil S Baran1.   

Abstract

The development of a new decarboxylative cross-coupling method that affords terminal and substituted alkynes from various carboxylic acids is described using both nickel- and iron-based catalysts. The use of N-hydroxytetrachlorophthalimide (TCNHPI) esters is crucial to the success of the transformation, and the reaction is amenable to in situ carboxylic acid activation. Additionally, an inexpensive, commercially available alkyne source is employed in this formal homologation process that serves as a surrogate for other well-established alkyne syntheses. The reaction is operationally simple and broad in scope while providing succinct and scalable avenues to previously reported synthetic intermediates.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynylation; homologation; iron catalysis; nickel catalysis; redox-active esters

Mesh：

Substances：

Year:  2017        PMID： 28636185      PMCID： PMC5792189          DOI： 10.1002/anie.201705107

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  39 in total

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Authors:  Chao Li; Jie Wang; Lisa M Barton; Shan Yu; Maoqun Tian; David S Peters; Manoj Kumar; Antony W Yu; Kristen A Johnson; Arnab K Chatterjee; Ming Yan; Phil S Baran
Journal:  Science       Date:  2017-04-13       Impact factor: 47.728

2.  The copper-catalyzed decarboxylative coupling of the sp3-hybridized carbon atoms of alpha-amino acids.

Authors:  Hai-Peng Bi; Liang Zhao; Yong-Min Liang; Chao-Jun Li
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Diastereoselective Cobalt-Mediated Cross-Couplings of Cycloalkyl Iodides with Alkynyl or (Hetero)Aryl Grignard Reagents.

Authors:  Jeffrey M Hammann; Diana Haas; Carl-Phillip Tüllmann; Konstantin Karaghiosoff; Paul Knochel
Journal:  Org Lett       Date:  2016-09-20       Impact factor: 6.005

4.  Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.

Authors:  Fahmi Himo; Timothy Lovell; Robert Hilgraf; Vsevolod V Rostovtsev; Louis Noodleman; K Barry Sharpless; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

Review 5.  Cu-free click cycloaddition reactions in chemical biology.

Authors:  John C Jewett; Carolyn R Bertozzi
Journal:  Chem Soc Rev       Date:  2010-04       Impact factor: 54.564

6.  Copper catalyzed decarboxylative alkynylation of quaternary α-cyano acetate salts.

Authors:  Yi-Si Feng; Zhong-Qiu Xu; Long Mao; Feng-Feng Zhang; Hua-Jian Xu
Journal:  Org Lett       Date:  2013-03-08       Impact factor: 6.005

7.  Room-temperature decarboxylative alkynylation of carboxylic acids using photoredox catalysis and EBX reagents.

Authors:  Franck Le Vaillant; Thibaut Courant; Jerome Waser
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-24       Impact factor: 15.336

8.  Domino process in silver-catalyzed reactions of N-arylformimidates and active methylene compounds involving cycloisomerization and 1,3-alkenyl shift.

Authors:  Chang Ho Oh; Swastik Karmakar; HyoSeung Park; YoungCheon Ahn; Jung Wook Kim
Journal:  J Am Chem Soc       Date:  2010-02-17       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

10.  Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides.

Authors:  Kierra M M Huihui; Jill A Caputo; Zulema Melchor; Astrid M Olivares; Amanda M Spiewak; Keywan A Johnson; Tarah A DiBenedetto; Seoyoung Kim; Laura K G Ackerman; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2016-04-11       Impact factor: 15.419
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  28 in total

1.  Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents.

Authors:  Tie-Gen Chen; Haolin Zhang; Pavel K Mykhailiuk; Rohan R Merchant; Courtney A Smith; Tian Qin; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-30       Impact factor: 15.336

2.  A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling.

Authors:  Shengyang Ni; Alberto F Garrido-Castro; Rohan R Merchant; Justine N de Gruyter; Daniel C Schmitt; James J Mousseau; Gary M Gallego; Shouliang Yang; Michael R Collins; Jennifer X Qiao; Kap-Sun Yeung; David R Langley; Michael A Poss; Paul M Scola; Tian Qin; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-15       Impact factor: 15.336

3.  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

4.  Reductive Decarboxylative Alkynylation of N-Hydroxyphthalimide Esters with Bromoalkynes.

Authors:  Liangbin Huang; Astrid M Olivares; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       Impact factor: 15.336

5.  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

6.  Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes.

Authors:  Anirudra Paul; N R Thimmegowda; Thiago Galani Cruz; Daniel Seidel
Journal:  Org Lett       Date:  2018-01-12       Impact factor: 6.005

7.  Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

Authors:  Cian Kingston; Michael A Wallace; Alban J Allentoff; Justine N deGruyter; Jason S Chen; Sharon X Gong; Samuel Bonacorsi; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-01-03       Impact factor: 15.419

8.  Radical Retrosynthesis.

Authors:  Joel M Smith; Stephen J Harwood; Phil S Baran
Journal:  Acc Chem Res       Date:  2018-08-02       Impact factor: 22.384

9.  CITU: A Peptide and Decarboxylative Coupling Reagent.

Authors:  Justine N deGruyter; Lara R Malins; Laurin Wimmer; Khalyd J Clay; Javier Lopez-Ogalla; Tian Qin; Josep Cornella; Zhiqing Liu; Guanda Che; Denghui Bao; Jason M Stevens; Jennifer X Qiao; Martin P Allen; Michael A Poss; Phil S Baran
Journal:  Org Lett       Date:  2017-11-08       Impact factor: 6.005

10.  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
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