Literature DB >> 22133348

Palladium-catalyzed C3-benzylation of indoles.

Ye Zhu1, Viresh H Rawal.   

Abstract

A general method for regioselective C3-benzylation of indoles has been developed. Various n class="Chemical">3-substituted indoles and benzyl methyl carbonates with different electronic properties react under mild conditions to afford a diverse range of 3-benzylindolenine products in good yields.
© 2011 American Chemical Society

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Year:  2011        PMID： 22133348      PMCID： PMC3383063          DOI： 10.1021/ja2095393

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  26 in total

1.  Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane.

Authors:  Masanari Kimura; Makoto Futamata; Ryutaro Mukai; Yoshinao Tamaru
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

Review 2.  Update 1 of: Synthesis and functionalization of indoles through palladium-catalyzed reactions.

Authors:  Sandro Cacchi; Giancarlo Fabrizi
Journal:  Chem Rev       Date:  2011-05-05       Impact factor: 60.622

3.  Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes.

Authors:  Barry M Trost; Jean Quancard
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

4.  A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

Authors:  Longyan Liao; Ranjan Jana; Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

5.  Decarboxylative benzylations of alkynes and ketones.

Authors:  Robert R P Torregrosa; Yamuna Ariyarathna; Kalicharan Chattopadhyay; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

6.  Palladium-catalyzed asymmetric benzylation of 3-aryl oxindoles.

Authors:  Barry M Trost; Lara C Czabaniuk
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

7.  An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine.

Authors:  Sergey A Kozmin; Tetsuo Iwama; Yong Huang; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

8.  New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic substitution: controlling the regioselectivity.

Authors:  Marco Bandini; Alfonso Melloni; Achille Umani-Ronchi
Journal:  Org Lett       Date:  2004-09-02       Impact factor: 6.005

9.  Palladium-catalyzed beta-allylation of 2,3-disubstituted indoles.

Authors:  Natsuko Kagawa; Jeremiah P Malerich; Viresh H Rawal
Journal:  Org Lett       Date:  2008-05-21       Impact factor: 6.005

10.  Activation and functionalization of benzylic derivatives by palladium catalysts.

Authors:  Benoît Liégault; Jean-Luc Renaud; Christian Bruneau
Journal:  Chem Soc Rev       Date:  2007-10-17       Impact factor: 54.564
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  18 in total

1.  Friedel-Crafts Alkylation of Indoles with Trichloroacetimidates.

Authors:  Tamie Suzuki; John D Chisholm
Journal:  Tetrahedron Lett       Date:  2019-04-03       Impact factor: 2.415

2.  Synthesis of 3,3'-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates.

Authors:  Arijit A Adhikari; Léa Radal; John D Chisholm
Journal:  Synlett       Date:  2017-07-11       Impact factor: 2.454

3.  Copper-catalyzed diastereoselective arylation of tryptophan derivatives: total synthesis of (+)-naseseazines A and B.

Authors:  Madeleine E Kieffer; Kangway V Chuang; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2013-04-03       Impact factor: 15.419

4.  An intramolecular cascade cyclization of 2-aryl indoles: efficient methods for the construction of 2,3-functionalized indolines and 3-indolinones.

Authors:  Arun K Ghosh; Zhi-Hua Chen
Journal:  Org Biomol Chem       Date:  2014-05-01       Impact factor: 3.876

5.  Pd-Catalyzed Alkene Carboheteroarylation Reactions for the Synthesis of 3-Cyclopentylindole Derivatives.

Authors:  Janelle K Kirsch; Jenna L Manske; John P Wolfe
Journal:  J Org Chem       Date:  2018-10-10       Impact factor: 4.354

6.  Palladium-catalyzed decarboxylative allylation and benzylation of N-alloc and N-Cbz indoles.

Authors:  Thomas D Montgomery; Ye Zhu; Natsuko Kagawa; Viresh H Rawal
Journal:  Org Lett       Date:  2013-02-21       Impact factor: 6.005

7.  Palladium-catalyzed, pyrrolidine-mediated arylmethylation of ketones and aldehydes with coumarinyl(methyl) acetates.

Authors:  Kalicharan Cattopadhyay; Antonio Recio; Jon A Tunge
Journal:  Org Biomol Chem       Date:  2012-07-25       Impact factor: 3.876

8.  A Copper-Catalyzed Arylation of Tryptamines for the Direct Synthesis of Aryl Pyrroloindolines.

Authors:  Madeleine E Kieffer; Kangway V Chuang; Sarah E Reisman
Journal:  Chem Sci       Date:  2012-11       Impact factor: 9.825

9.  Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles.

Authors:  Kalicharan Chattopadhyay; Erik Fenster; Alexander J Grenning; Jon A Tunge
Journal:  Beilstein J Org Chem       Date:  2012-07-27       Impact factor: 2.883

10.  Ortho-aryl substituted DPEphos ligands: rhodium complexes featuring C-H anagostic interactions and B-H agostic bonds.

Authors:  James J Race; Arron L Burnage; Timothy M Boyd; Alex Heyam; Antonio J Martínez-Martínez; Stuart A Macgregor; Andrew S Weller
Journal:  Chem Sci       Date:  2021-05-25       Impact factor: 9.825
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