Literature DB >> 23941443

C-H functionalization of cyclopropanes: a practical approach employing a picolinamide auxiliary.

Daniela Sustac Roman1, André B Charette.   

Abstract

A Pd-catalyzed, picolinamide-enabled, and efficient C-H arylation of cyclopropanes is described. The reaction can be promoted by either a silver additive or catalytic pivalic acid in the presence of a carbonate base. Various aryl iodides can be employed as coupling partners, providing exclusively cis-substituted cyclopropylpicolinamides.

Entities:  

Year:  2013        PMID： 23941443     DOI： 10.1021/ol401931s

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


  8 in total

1.  Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors:  Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal:  Chem Rev       Date:  2016-12-02       Impact factor: 60.622

2.  Enantio- and Diastereoswitchable C-H Arylation of Methylene Groups in Cycloalkanes.

Authors:  Michal S Andrä; Lukas Schifferer; Corina H Pollok; Christian Merten; Lukas J Gooßen; Jin-Quan Yu
Journal:  Chemistry       Date:  2019-05-27       Impact factor: 5.236

Review 3.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

4.  Palladium-Catalyzed Directed C(sp3)-H Arylation of Saturated Heterocycles at C-3 Using a Concise Optimization Approach.

Authors:  Dominic P Affron; James A Bull
Journal:  European J Org Chem       Date:  2015-11-27

5.  Palladium-catalyzed picolinamide-directed iodination of remote ortho-C-H bonds of arenes: Synthesis of tetrahydroquinolines.

Authors:  William A Nack; Xinmou Wang; Bo Wang; Gang He; Gong Chen
Journal:  Beilstein J Org Chem       Date:  2016-06-17       Impact factor: 2.883

6.  Enantioselective palladium(0)-catalyzed intramolecular cyclopropane functionalization: access to dihydroquinolones, dihydroisoquinolones and the BMS-791325 ring system.

Authors:  J Pedroni; T Saget; P A Donets; N Cramer
Journal:  Chem Sci       Date:  2015-06-17       Impact factor: 9.825

7.  Divergent Synthesis of Cyclopropane-Containing Lead-Like Compounds, Fragments and Building Blocks through a Cobalt Catalyzed Cyclopropanation of Phenyl Vinyl Sulfide.

Authors:  Stephen J Chawner; Manuel J Cases-Thomas; James A Bull
Journal:  European J Org Chem       Date:  2017-09-11

8.  C-H Activation Enables a Concise Total Synthesis of Quinine and Analogues with Enhanced Antimalarial Activity.

Authors:  Daniel H O' Donovan; Paul Aillard; Martin Berger; Aurélien de la Torre; Desislava Petkova; Christian Knittl-Frank; Danny Geerdink; Marcel Kaiser; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-22       Impact factor: 16.823
  8 in total

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