Literature DB >> 22447100

Progress in palladium-based catalytic systems for the sustainable synthesis of annulated heterocycles: a focus on indole backbones.

Mélanie Platon1, Régine Amardeil, Laurent Djakovitch, Jean-Cyrille Hierso.   

Abstract

A survey highlighting the most recent palladium catalytic systems produced and their performances for progress in direct synthesis of indole backbones by heterocarbocyclization of reactive substrates is provided. The discussion is developed in relation with the principles of sustainable chemistry concerning atom and mass economy. In this respect, the general convergent character of the syntheses is of particular interest (one-pot, domino, cascade or tandem reactions), and the substrates accessibility and reactivity, together with the final waste production, are also important. This critical review clearly indicates that the development of ligand chemistry, mainly phosphines and carbenes, in the last few decades gave a significant impetus to powerful functionalization of indoles at virtually all positions of this ubiquitous backbone (118 references).

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Year:  2012        PMID: 22447100     DOI: 10.1039/c2cs15350e

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  24 in total

1.  Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C-H Coupling of Arylamines with 1,2- and 1,3-Diols.

Authors:  Hanbin Lee; Chae S Yi
Journal:  Organometallics       Date:  2016-05-27       Impact factor: 3.876

2.  Divergent Reactivity of Rhodium(I) Carbenes Derived from Indole Annulations.

Authors:  Xiaoxun Li; Hui Li; Wangze Song; Po-Sen Tseng; Lingyan Liu; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-07       Impact factor: 15.336

3.  N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles.

Authors:  M Todd Hovey; Christopher T Check; Alexandra F Sipher; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-14       Impact factor: 15.336

4.  Benzannulation via the reaction of ynamides and vinylketenes. application to the synthesis of highly substituted indoles.

Authors:  Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
Journal:  J Org Chem       Date:  2013-09-03       Impact factor: 4.354

5.  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

6.  Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles: substrate scope and mechanistic investigation.

Authors:  M Alexander Düfert; Kelvin L Billingsley; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2013-08-16       Impact factor: 15.419

7.  Platinum-catalyzed tandem indole annulation/arylation for the synthesis of diindolylmethanes and indolo[3,2-b]carbazoles.

Authors:  Dongxu Shu; Gabrielle N Winston-McPherson; Wangze Song; Weiping Tang
Journal:  Org Lett       Date:  2013-08-05       Impact factor: 6.005

8.  Computational study of Ru-catalyzed cycloisomerization of 2-alkynylanilides.

Authors:  Xinghui Zhang; Shanshan Li; Xiaoli Wei; Yun Lei
Journal:  J Mol Model       Date:  2018-06-14       Impact factor: 1.810

9.  Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols.

Authors:  Hui Li; Xiaoxun Li; Hao-Yuan Wang; Gabrielle N Winston-McPherson; Hao-miao Julie Geng; Ilia A Guzei; Weiping Tang
Journal:  Chem Commun (Camb)       Date:  2014-10-21       Impact factor: 6.222

10.  Rhodium(I)-Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles.

Authors:  Xiaoxun Li; Haibo Xie; Xiaoning Fu; Ji-Tian Liu; Hao-Yuan Wang; Bao-Min Xi; Peng Liu; Xiufang Xu; Weiping Tang
Journal:  Chemistry       Date:  2016-06-20       Impact factor: 5.236

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