Literature DB >> 20024323

Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems.

Natalia Chernyak1, David Tilly, Zhou Li, Vladimir Gevorgyan.   

Abstract

Polycyclic indole structures, possessing fused seven-membered rings were efficiently synthesized via the Pd-catalyzed intramolecular carbopalladation-annulation of 3-(2-iodobenzyl)-indoles and alkynes. A remarkable base effect on the chemoselectivity of this transformation has been found: switching from Et(3)N to CsOAc completely reverses the reaction path to intramolecular cyclization forming fused five-membered rings.

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Year:  2009        PMID： 20024323      PMCID： PMC3690920          DOI： 10.1039/b919991h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  21 in total

1.  New cascade 2-indolylacyl radical addition-cyclization reactions.

Authors:  M L Bennasar; T Roca; R Griera; J Bosch
Journal:  J Org Chem       Date:  2001-11-02       Impact factor: 4.354

Review 2.  Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Authors:  Dino Alberico; Mark E Scott; Mark Lautens
Journal:  Chem Rev       Date:  2007-01       Impact factor: 60.622

Review 3.  Simple indole alkaloids and those with a nonrearranged monoterpenoid unit.

Authors:  Kazuhiro Higuchi; Tomomi Kawasaki
Journal:  Nat Prod Rep       Date:  2007-03-23       Impact factor: 13.423

4.  Direct Pd-catalyzed arylation of 1,2,3-triazoles.

Authors:  Stepan Chuprakov; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2007-05-10       Impact factor: 6.005

5.  A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction.

Authors:  Cyril Bressy; Dino Alberico; Mark Lautens
Journal:  J Am Chem Soc       Date:  2005-09-28       Impact factor: 15.419

6.  Catalytic direct arylation with aryl chlorides, bromides, and iodides: intramolecular studies leading to new intermolecular reactions.

Authors:  Louis-Charles Campeau; Mathieu Parisien; Annie Jean; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2006-01-18       Impact factor: 15.419

7.  Phosphine-free palladium-catalyzed C-H bond arylation of free (N-H)-indoles and pyrroles.

Authors:  Xiang Wang; Denis V Gribkov; Dalibor Sames
Journal:  J Org Chem       Date:  2007-02-16       Impact factor: 4.354

8.  Synthesis of heterocycles via palladium pi-olefin and pi-alkyne chemistry.

Authors:  Gilson Zeni; Richard C Larock
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

9.  Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling.

Authors:  David R Stuart; Elisia Villemure; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2007-09-19       Impact factor: 15.419

10.  Proton-abstraction mechanism in the palladium-catalyzed intramolecular arylation: substituent effects.

Authors:  Domingo García-Cuadrado; Paula de Mendoza; Ataualpa A C Braga; Feliu Maseras; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2007-04-27       Impact factor: 15.419
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  4 in total

1.  Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes.

Authors:  Liene Grigorjeva; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-24       Impact factor: 15.336

2.  Cobalt-Catalyzed, Aminoquinoline-Directed Functionalization of Phosphinic Amide sp2 C-H Bonds.

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  ACS Catal       Date:  2015-12-22       Impact factor: 13.084

3.  Cascade carbopalladation-annulation approach toward polycylic derivatives of indole and indolizine.

Authors:  Natalia Chernyak; David Tilly; Zhou Li; Vladimir Gevorgyan
Journal:  ARKIVOC       Date:  2010-12-10       Impact factor: 1.140

4.  New Reactions of Contraction of the o-Quinone Ring with the Formation of Derivatives of 2-(2-Indolyl)-cyclopenta[b]pyrrole-3,4-diones and Pyrindino[1,2-a]indoles: A Combined Experimental and Density Functional Theory Investigation.

Authors:  Yurii A Sayapin; Igor V Dorogan; Evgeny A Gusakov; Duong Nghia Bang; Valery V Tkachev; Inna Olegovna Tupaeva; Dai Lam Tran; Trang Van Nguyen; Toan Ngoc Duong; Hoang Vu Dinh; Tatyana A Krasnikova; Serguei M Aldoshin; Vladimir I Minkin
Journal:  ACS Omega       Date:  2021-07-08
  4 in total

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