Literature DB >> 29993084

C-H alkylation reactions of indoles mediated by Pd(ii) and norbornene: applications and recent developments.

Marcus Wegmann1, Michael Henkel, Thorsten Bach.   

Abstract

The Catellani reaction enables an ortho-C-H activation based on oxidative addition of Pd(0) and an intermediary carbopalladation of norbornene. Among its variants, the recently developed C2-selective alkylation of indoles is particular as it employs Pd(ii) as the source of palladium. This review describes the mechanistic background of this transformation. Applications in total synthesis and in the synthesis of biologically relevant molecules are illustrated and further developments of the method are discussed.

Entities:  

Year:  2018        PMID: 29993084     DOI: 10.1039/c8ob01025k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  11 in total

1.  Palladium/Norbornene Cooperative Catalysis.

Authors:  Jianchun Wang; Guangbin Dong
Journal:  Chem Rev       Date:  2019-04-25       Impact factor: 60.622

2.  Rapid Access to Multisubstituted Acrylamides from Cyclic Ketones via Palladium/Norbornene Cooperative Catalysis.

Authors:  Zhao Wu; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-04       Impact factor: 15.336

3.  Redox-Neutral Vicinal Difunctionalization of Five-Membered Heteroarenes with Dual Electrophiles.

Authors:  Renhe Li; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-10       Impact factor: 15.336

4.  Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C─H activation.

Authors:  Alexander J Rago; Guangbin Dong
Journal:  Green Synth Catal       Date:  2021-03-04

Review 5.  Structurally Modified Norbornenes: A Key Factor to Modulate Reaction Selectivity in the Palladium/Norbornene Cooperative Catalysis.

Authors:  Renhe Li; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2020-10-05       Impact factor: 15.419

6.  Unexpected ortho-Heck Reaction under the Catellani Conditions.

Authors:  Alexander J Rago; Guangbin Dong
Journal:  Org Lett       Date:  2020-04-02       Impact factor: 6.005

7.  Synthesis of C3,C4-Disubstituted Indoles via the Palladium/Norbornene-Catalyzed ortho-Amination/ipso-Heck Cyclization.

Authors:  Alexander J Rago; Guangbin Dong
Journal:  Org Lett       Date:  2021-04-26       Impact factor: 6.072

8.  Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3-Chloroindolenines.

Authors:  Jordy M Saya; Ellen D H van Wordragen; Romano V A Orru; Eelco Ruijter
Journal:  European J Org Chem       Date:  2019-01-17

9.  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

Review 10.  Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C-H Functionalization.

Authors:  Zhenbo Yuan; Xuanzhong Liu; Changmei Liu; Yan Zhang; Yijian Rao
Journal:  Molecules       Date:  2020-11-12       Impact factor: 4.411

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