Literature DB >> 18393521

Palladium-catalyzed sp(3) CH activation of simple alkyl groups: direct preparation of indoline derivatives from N-alkyl-2-bromoanilines.

Toshiaki Watanabe1, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno.   

Abstract

The sp3 C-H activation of a simple alkyl group catalyzed by palladium(0) provides a novel and convenient strategy for the synthesis of various indolines from simple precursors, such as N-alkyl-2-bromoanilines. This study demonstrates that assisting moieties in the substrate such as a pyridine or quaternary carbon are not always necessary for sp3 C-H activation.

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Year:  2008        PMID: 18393521     DOI: 10.1021/ol800425z

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


  25 in total

1.  Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Authors:  Tian-Sheng Mei; Lei Kou; Sandy Ma; Keary M Engle; Jin-Quan Yu
Journal:  Synthesis (Stuttg)       Date:  2012-05-25       Impact factor: 3.157

2.  Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

3.  Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction.

Authors:  Ana Minatti; Stephen L Buchwald
Journal:  Org Lett       Date:  2008-06-04       Impact factor: 6.005

4.  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

5.  Fluorenone synthesis by palladacycle-catalyzed sequential reactions of 2-bromobenzaldehydes with arylboronic acids.

Authors:  Tao-Ping Liu; Yuan-Xi Liao; Chun-Hui Xing; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2011-04-11       Impact factor: 6.005

Review 6.  Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-05       Impact factor: 15.336

7.  Heterocycle synthesis via direct C-H/N-H coupling.

Authors:  Enrico T Nadres; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-12-29       Impact factor: 15.419

8.  Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

Authors:  Enrico T Nadres; Gerson Ivan Franco Santos; Dmitry Shabashov; Olafs Daugulis
Journal:  J Org Chem       Date:  2013-09-19       Impact factor: 4.354

9.  Pd(0)-catalyzed sequential C-N bond formation via allylic and aromatic C-H amination of α-methylstyrenes with diaziridinone.

Authors:  Thomas A Ramirez; Qian Wang; Yingguang Zhu; Huaiji Zheng; Xingao Peng; Richard G Cornwall; Yian Shi
Journal:  Org Lett       Date:  2013-08-06       Impact factor: 6.005

10.  Pd(0)/PR3-catalyzed intermolecular arylation of sp3 C-H bonds.

Authors:  Masayuki Wasa; Keary M Engle; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

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