Literature DB >> 33727973

Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes.

Olga Bakhanovich1,2, Viktor Khutorianskyi1, Vladimir Motornov1, Petr Beier1.   

Abstract

The rhodium-catalyzed transannulation of N-perfluoroalkyl-1,2,3-triazoles with aromatic and aliphatic terminal alkynes under microwave heating conditions afforded N-perfluoroalkyl-3,4-disubstituted pyrroles (major products) and N-fluoroalkyl-2,4-disubstituted pyrroles (minor products). The observed selectivities in the case of the reactions with aliphatic alkynes were high.
Copyright © 2021, Bakhanovich et al.

Entities:  

Keywords:  pyrrole; rhodium carbene; transannulation; triazole

Year:  2021        PMID： 33727973      PMCID： PMC7934709          DOI： 10.3762/bjoc.17.44

Source DB:  PubMed          Journal:  Beilstein J Org Chem        ISSN： 1860-5397            Impact factor:   2.883


  20 in total

Review 1.  Transition-metal-catalyzed denitrogenative transannulation: converting triazoles into other heterocyclic systems.

Authors:  Buddhadeb Chattopadhyay; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-25       Impact factor: 15.336

Review 2.  Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II-III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas.

Authors:  Yu Zhou; Jiang Wang; Zhanni Gu; Shuni Wang; Wei Zhu; José Luis Aceña; Vadim A Soloshonok; Kunisuke Izawa; Hong Liu
Journal:  Chem Rev       Date:  2016-01-12       Impact factor: 60.622

Review 3.  Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.

Authors:  Nicholas A Meanwell
Journal:  J Med Chem       Date:  2018-02-05       Impact factor: 7.446

4.  Rhodium(II)-Catalyzed Formal [3 + 2] Cycloaddition of N-Sulfonyl-1,2,3-triazoles with Isoxazoles: Entry to Polysubstituted 3-Aminopyrroles.

Authors:  Xiaoqiang Lei; Longbo Li; Yu-Peng He; Yefeng Tang
Journal:  Org Lett       Date:  2015-10-15       Impact factor: 6.005

5.  Azidoperfluoroalkanes: Synthesis and Application in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition.

Authors:  Zsófia E Blastik; Svatava Voltrová; Václav Matoušek; Bronislav Jurásek; David W Manley; Blanka Klepetářová; Petr Beier
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-05       Impact factor: 15.336

6.  DFT Mechanistic Study of Rh(III)-Catalyzed [3 + 2]/[5 + 2] Annulation of 4-Aryl-1,2,3-triazoles and Alkynes Unveils the Dual C-H Activation Strategy.

Authors:  Zhongchao Zhang; Shengwen Yang; Juan Li; Xiaojian Liao
Journal:  J Org Chem       Date:  2016-10-12       Impact factor: 4.354

7.  Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles.

Authors:  Huw M L Davies; Joshua S Alford
Journal:  Chem Soc Rev       Date:  2014-08-07       Impact factor: 54.564

8.  Rhodium-catalyzed conversion of furans to highly functionalized pyrroles.

Authors:  Brendan T Parr; Samantha A Green; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2013-03-14       Impact factor: 15.419

9.  Regiocontrolled synthesis of polysubstituted pyrroles starting from terminal alkynes, sulfonyl azides, and allenes.

Authors:  Tomoya Miura; Kentaro Hiraga; Tsuneaki Biyajima; Takayuki Nakamuro; Masahiro Murakami
Journal:  Org Lett       Date:  2013-06-18       Impact factor: 6.005

Review 10.  Fluorine in medicinal chemistry.

Authors:  Sophie Purser; Peter R Moore; Steve Swallow; Véronique Gouverneur
Journal:  Chem Soc Rev       Date:  2007-12-13       Impact factor: 54.564
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