Literature DB >> 25972069

Rh(III)-Catalyzed C-H Alkylation of Arenes Using Alkylboron Reagents.

He Wang1, Songjie Yu1, Zisong Qi1, Xingwei Li1.   

Abstract

Rhodium(III)-catalyzed direct alkylation of arenes using commercially available alkyltrifluoroborates is disclosed. Oximes, heteroarenes, azomethines, N-nitrosoamines, and amides are viable directing groups to entail this transformation. The alkyl group in the boron reagent can be extended to primary alkyls, benzyl, and cycloalkyls, and the reaction proceeded with controllable mono- and dialkylation selectivity when both ortho C-H sites are accessible.

Entities:  

Year:  2015        PMID: 25972069     DOI: 10.1021/acs.orglett.5b01232

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


  6 in total

1.  Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration.

Authors:  Veronika M Shoba; Nathan C Thacker; Andrew J Bochat; James M Takacs
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-10       Impact factor: 15.336

Review 2.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

3.  Merging rhodium-catalysed C-H activation and hydroamination in a highly selective [4+2] imine/alkyne annulation.

Authors:  Rajith S Manan; Pinjing Zhao
Journal:  Nat Commun       Date:  2016-06-20       Impact factor: 14.919

4.  Rhoda-Electrocatalyzed C-H Methylation and Paired Electrocatalyzed C-H Ethylation and Propylation.

Authors:  Krzysztof Kuciński; Hendrik Simon; Lutz Ackermann
Journal:  Chemistry       Date:  2021-11-10       Impact factor: 5.020

5.  Palladium-catalyzed nucleomethylation of alkynes for synthesis of methylated heteroaromatic compounds.

Authors:  Xi Yang; Gang Wang; Zhi-Shi Ye
Journal:  Chem Sci       Date:  2022-08-18       Impact factor: 9.969

6.  Nickel-catalyzed C-H alkylation of indoles with unactivated alkyl chlorides: evidence of a Ni(i)/Ni(iii) pathway.

Authors:  Dilip K Pandey; Shidheshwar B Ankade; Abad Ali; C P Vinod; Benudhar Punji
Journal:  Chem Sci       Date:  2019-08-19       Impact factor: 9.825

  6 in total

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