Literature DB >> 28375631

Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides.

Naoyuki Suzuki1, Julie L Hofstra1, Kelsey E Poremba1, Sarah E Reisman1.   

Abstract

An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetrakis(N,N-dimethylamino)ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with >90% ee.

Entities:  

Mesh：

Substances：

Year:  2017        PMID： 28375631      PMCID： PMC5868419          DOI： 10.1021/acs.orglett.7b00793

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  46 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Amino alcohols as ligands for nickel-catalyzed suzuki reactions of unactivated alkyl halides, including secondary alkyl chlorides, with arylboronic acids.

Authors:  Francisco González-Bobes; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2006-04-26       Impact factor: 15.419

Review 3.  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

4.  Direct Acylation of C(sp(3))-H Bonds Enabled by Nickel and Photoredox Catalysis.

Authors:  Candice L Joe; Abigail G Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-17       Impact factor: 15.336

5.  Nickel-catalyzed reductive cross-coupling of unactivated alkyl halides.

Authors:  Xiaolong Yu; Tao Yang; Shulin Wang; Hailiang Xu; Hegui Gong
Journal:  Org Lett       Date:  2011-03-24       Impact factor: 6.005

6.  Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

Authors:  Pamela M Lundin; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

7.  Ni- or Cu-catalyzed cross-coupling reaction of alkyl fluorides with Grignard reagents.

Authors:  Jun Terao; Aki Ikumi; Hitoshi Kuniyasu; Nobuaki Kambe
Journal:  J Am Chem Soc       Date:  2003-05-14       Impact factor: 15.419

8.  Functional group tolerant Kumada-Corriu-Tamao coupling of nonactivated alkyl halides with aryl and heteroaryl nucleophiles: catalysis by a nickel pincer complex permits the coupling of functionalized Grignard reagents.

Authors:  Oleg Vechorkin; Valérie Proust; Xile Hu
Journal:  J Am Chem Soc       Date:  2009-07-22       Impact factor: 15.419

9.  Cross-couplings of unactivated secondary alkyl halides: room-temperature nickel-catalyzed Negishi reactions of alkyl bromides and iodides.

Authors:  Jianrong Steve Zhou; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2003-12-03       Impact factor: 15.419

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
View more
  22 in total

1.  Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling.

Authors:  Julie L Hofstra; Alan H Cherney; Ciara M Ordner; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2017-12-20       Impact factor: 15.419

2.  Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement.

Authors:  Wei Zhao; Ryan P Wurz; Jonas C Peters; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2017-08-25       Impact factor: 15.419

3.  Synthesis of Chiral Bisoxazoline Ligands: (3aR,3a'R,8aS,8a'S)-2,2'-(cyclopropane-1,1-diyl)bis(3a,8adihydro-8H-indeno[1,2-d]oxazole).

Authors:  Julie L Hofstra; Travis J DeLano; Sarah E Reisman
Journal:  Organic Synth       Date:  2020-08-20

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.  Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions.

Authors:  Kelsey E Poremba; Sara E Dibrell; Sarah E Reisman
Journal:  ACS Catal       Date:  2020-06-24       Impact factor: 13.084

6.  Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides.

Authors:  Julie L Hofstra; Kelsey E Poremba; Alex M Shimozono; Sarah E Reisman
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-19       Impact factor: 15.336

7.  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

8.  Evolution of a Strategy for the Enantioselective Synthesis of (-)-Cajanusine.

Authors:  Renyu Guo; Brittany P Witherspoon; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2020-03-09       Impact factor: 15.419

9.  Enantioselective Hydroalkenylation of Olefins with Enol Sulfonates Enabled by Dual Copper Hydride and Palladium Catalysis.

Authors:  Alexander W Schuppe; James Levi Knippel; Gustavo M Borrajo-Calleja; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2021-03-30       Impact factor: 15.419

10.  The Asymmetric Synthesis of Amines via Nickel-Catalyzed Enantioconvergent Substitution Reactions.

Authors:  Ze-Peng Yang; Dylan J Freas; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2021-02-10       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.