Literature DB >> 30206614

Copper-boryl mediated organic synthesis.

David Hemming1, Russell Fritzemeier, Stephen A Westcott, Webster L Santos, Patrick G Steel.   

Abstract

Organoboron compounds are valuable synthetic intermediates that find application in a diverse variety of processes including both C-X and C-C bond-forming transformations. This has been achieved by using a variety of boron derivatives. Of these, boronate esters are probably the most versatile and, reflecting this, methods for the generation of boronate esters are of considerable current interest. Given the mild reaction conditions, good functional group tolerance, and low cost of the metal catalyst, the use of copper-boryl reagents is particularly attractive. In this review, methodologies in copper-boryl chemistry are discussed and the many different transformations possible are surveyed.

Entities:  

Year:  2018        PMID: 30206614     DOI: 10.1039/c7cs00816c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  31 in total

1.  Tuning the copper(II)/copper(I) redox potential for more robust copper-catalyzed C-N bond forming reactions.

Authors:  James D Cope; Henry U Valle; Ruby S Hall; Kathleen M Riley; Ekta Goel; Saborni Biswas; Michael P Hendrich; David O Wipf; Sean L Stokes; Joseph P Emerson
Journal:  Eur J Inorg Chem       Date:  2020-02-26       Impact factor: 2.524

2.  Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies.

Authors:  Stephen R Sardini; Alison L Lambright; Grace L Trammel; Humair M Omer; Peng Liu; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2019-06-04       Impact factor: 15.419

3.  Racemic Vinylallenes in Catalytic Enantioselective Multicomponent Processes: Rapid Generation of Complexity through 1,6-Conjugate Additions.

Authors:  Youming Huang; Sebastian Torker; Xinghan Li; Juan Del Pozo; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-06       Impact factor: 15.336

4.  Catalyst-Controlled 1,2- and 1,1-Arylboration of α-Alkyl Alkenyl Arenes.

Authors:  Allison M Bergmann; Stanna K Dorn; Kevin B Smith; Kaitlyn M Logan; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-09       Impact factor: 15.336

5.  Multifaceted Substrate-Ligand Interactions Promote the Copper-Catalyzed Hydroboration of Benzylidenecyclobutanes and Related Compounds.

Authors:  Taeho Kang; Tuğçe G Erbay; Kane L Xu; Gary M Gallego; Alexander Burtea; Sajiv K Nair; Ryan L Patman; Ru Zhou; Scott C Sutton; Indrawan J McAlpine; Peng Liu; Keary M Engle
Journal:  ACS Catal       Date:  2020-10-27       Impact factor: 13.084

6.  Low-Valent Tungsten Catalysis Enables Site-Selective Isomerization-Hydroboration of Unactivated Alkenes.

Authors:  Tanner C Jankins; Raul Martin-Montero; Phillippa Cooper; Ruben Martin; Keary M Engle
Journal:  J Am Chem Soc       Date:  2021-09-09       Impact factor: 16.383

7.  Synthesis of Bisheteroarylalkanes by Heteroarylboration: Development and Application of a Pyridylidene-Copper Complex.

Authors:  Yuan Huang; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-27       Impact factor: 15.336

8.  Streamlined Catalytic Enantioselective Synthesis of α-Substituted β,γ-Unsaturated Ketones and Either of the Corresponding Tertiary Homoallylic Alcohol Diastereomers.

Authors:  Juan Del Pozo; Shaochen Zhang; Filippo Romiti; Shibo Xu; Ryan P Conger; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2020-10-05       Impact factor: 15.419

Review 9.  Copper-catalyzed functionalization of enynes.

Authors:  Quentin Dherbassy; Srimanta Manna; Fabien J T Talbot; Watcharapon Prasitwatcharakorn; Gregory J P Perry; David J Procter
Journal:  Chem Sci       Date:  2020-10-07       Impact factor: 9.825

10.  Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes*.

Authors:  Yang Gao; Sima Yazdani; Aaron Kendrick; Glen P Junor; Taeho Kang; Douglas B Grotjahn; Guy Bertrand; Rodolphe Jazzar; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-29       Impact factor: 16.823

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