Literature DB >> 27981703

Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms.

Tian Qin1, Lara R Malins1, Jacob T Edwards1, Rohan R Merchant1, Alexander J E Novak1, Jacob Z Zhong1, Riley B Mills1, Ming Yan1, Changxia Yuan2, Martin D Eastgate2, Phil S Baran1.   

Abstract

Two named reactions of fundamental importance and paramount utility in organic synthesis have been reinvestigated, the Barton decarboxylation and Giese radical conjugate addition. N-hydroxyphthalimide (NHPI) based redox-active esters were found to be convenient starting materials for simple, thermal, Ni-catalyzed radical formation and subsequent trapping with either a hydrogen atom source (PhSiH3 ) or an electron-deficient olefin. These reactions feature operational simplicity, inexpensive reagents, and enhanced scope as evidenced by examples in the realm of peptide chemistry.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  conjugate addition; decarboxylation; esters; nickel catalysis; redox-active

Mesh：

Substances：

Year:  2016        PMID： 27981703      PMCID： PMC5295468          DOI： 10.1002/anie.201609662

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


  27 in total

Review 1.  Contemporary strategies for peptide macrocyclization.

Authors:  Christopher J White; Andrei K Yudin
Journal:  Nat Chem       Date:  2011-06-23       Impact factor: 24.427

2.  Posttranslational mutagenesis: A chemical strategy for exploring protein side-chain diversity.

Authors:  Tom H Wright; Ben J Bower; Justin M Chalker; Gonçalo J L Bernardes; Rafal Wiewiora; Wai-Lung Ng; Ritu Raj; Sarah Faulkner; M Robert J Vallée; Anuchit Phanumartwiwath; Oliver D Coleman; Marie-Laëtitia Thézénas; Maola Khan; Sébastien R G Galan; Lukas Lercher; Matthew W Schombs; Stefanie Gerstberger; Maria E Palm-Espling; Andrew J Baldwin; Benedikt M Kessler; Timothy D W Claridge; Shabaz Mohammed; Benjamin G Davis
Journal:  Science       Date:  2016-09-22       Impact factor: 47.728

Review 3.  Peptide stapling techniques based on different macrocyclisation chemistries.

Authors:  Yu Heng Lau; Peterson de Andrade; Yuteng Wu; David R Spring
Journal:  Chem Soc Rev       Date:  2014-09-08       Impact factor: 54.564

4.  Total synthesis guided structure elucidation of (+)-psychotetramine.

Authors:  Klement Foo; Timothy Newhouse; Ikue Mori; Hiromitsu Takayama; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-17       Impact factor: 15.336

5.  Reducing the cost, smell, and toxicity of the Barton reductive decarboxylation: chloroform as the hydrogen atom source.

Authors:  Eun Jung Ko; G Paul Savage; Craig M Williams; John Tsanaktsidis
Journal:  Org Lett       Date:  2011-03-25       Impact factor: 6.005

6.  Cyclopropylazetoindolines as precursors to C(3)-quaternary-substituted indolines.

Authors:  Vinson R Espejo; Xi-Bo Li; Jon D Rainier
Journal:  J Am Chem Soc       Date:  2010-06-23       Impact factor: 15.419

7.  Total Synthesis of Crotophorbolone.

Authors:  Taro Asaba; Yuki Katoh; Daisuke Urabe; Masayuki Inoue
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-23       Impact factor: 15.336

8.  Chloroform as a hydrogen atom donor in Barton reductive decarboxylation reactions.

Authors:  Junming Ho; Jingjing Zheng; Rubén Meana-Pañeda; Donald G Truhlar; Eun Jung Ko; G Paul Savage; Craig M Williams; Michelle L Coote; John Tsanaktsidis
Journal:  J Org Chem       Date:  2013-06-24       Impact factor: 4.354

9.  Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids.

Authors:  Jie Wang; Tian Qin; Tie-Gen Chen; Laurin Wimmer; Jacob T Edwards; Josep Cornella; Benjamin Vokits; Scott A Shaw; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-06       Impact factor: 15.336

10.  Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin.

Authors:  Lingling Chu; Chisa Ohta; Zhiwei Zuo; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2014-07-28       Impact factor: 15.419
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  43 in total

1.  Decarboxylative Alkynylation.

Authors:  Joel M Smith; Tian Qin; Rohan R Merchant; Jacob T Edwards; Lara R Malins; Zhiqing Liu; Guanda Che; Zichao Shen; Scott A Shaw; Martin D Eastgate; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-01       Impact factor: 15.336

2.  Decarboxylative borylation.

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

3.  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

4.  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

5.  Direct Access to Versatile Electrophiles via Catalytic Oxidative Cyanation of Alkenes.

Authors:  De-Wei Gao; Ekaterina V Vinogradova; Sri Krishna Nimmagadda; Jose M Medina; Yiyang Xiao; Radu M Suciu; Benjamin F Cravatt; Keary M Engle
Journal:  J Am Chem Soc       Date:  2018-06-22       Impact factor: 15.419

6.  Kinetically guided radical-based synthesis of C(sp3)-C(sp3) linkages on DNA.

Authors:  Jie Wang; Helena Lundberg; Shota Asai; Pedro Martín-Acosta; Jason S Chen; Stephen Brown; William Farrell; Russell G Dushin; Christopher J O'Donnell; Anokha S Ratnayake; Paul Richardson; Zhiqing Liu; Tian Qin; Donna G Blackmond; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2018-06-26       Impact factor: 11.205

7.  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

8.  2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

Authors:  Kangnan Li; Xinxin Shao; Luke Tseng; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

9.  Intermolecular Heck Coupling with Hindered Alkenes Directed by Potassium Carboxylates.

Authors:  Tucker R Huffman; Yebin Wu; Alexis Emmerich; Ryan A Shenvi
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-25       Impact factor: 15.336

10.  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
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