Literature DB >> 23344449

A sustainable catalytic pyrrole synthesis.

Stefan Michlik1, Rhett Kempe.   

Abstract

The pyrrole heterocycle is a prominent chemical motif and is found widely in natural products, drugs, catalysts and advanced materials. Here we introduce a sustainable iridium-catalysed pyrrole synthesis in which secondary alcohols and amino alcohols are deoxygenated and linked selectively via the formation of C-N and C-C bonds. Two equivalents of hydrogen gas are eliminated in the course of the reaction, and alcohols based entirely on renewable resources can be used as starting materials. The catalytic synthesis protocol tolerates a large variety of functional groups, which includes olefins, chlorides, bromides, organometallic moieties, amines and hydroxyl groups. We have developed a catalyst that operates efficiently under mild conditions.

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Year:  2013        PMID: 23344449     DOI: 10.1038/nchem.1547

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  24 in total

1.  Dye-sensitized solar cells.

Authors:  Anders Hagfeldt; Gerrit Boschloo; Licheng Sun; Lars Kloo; Henrik Pettersson
Journal:  Chem Rev       Date:  2010-09-10       Impact factor: 60.622

2.  Materials science. Toward flexible batteries.

Authors:  Hiroyuki Nishide; Kenichi Oyaizu
Journal:  Science       Date:  2008-02-08       Impact factor: 47.728

3.  Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles.

Authors:  Gabriela Guillena; Diego J Ramón; Miguel Yus
Journal:  Chem Rev       Date:  2010-03-10       Impact factor: 60.622

4.  Synthesis of peptides and pyrazines from β-amino alcohols through extrusion of H2 catalyzed by ruthenium pincer complexes: ligand-controlled selectivity.

Authors:  Boopathy Gnanaprakasam; Ekambaram Balaraman; Yehoshoa Ben-David; David Milstein
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-26       Impact factor: 15.336

5.  Pyrrole synthesis via allylic sp3 C-H activation of enamines followed by intermolecular coupling with unactivated alkynes.

Authors:  Souvik Rakshit; Frederic W Patureau; Frank Glorius
Journal:  J Am Chem Soc       Date:  2010-07-21       Impact factor: 15.419

6.  Copper-catalyzed tandem reactions of 1-(2-iodoary)-2-yn-1-ones with isocyanides for the synthesis of 4-oxo-indeno[1,2-b]pyrroles.

Authors:  Qian Cai; Fengtao Zhou; Tianfeng Xu; Liangbing Fu; Ke Ding
Journal:  Org Lett       Date:  2010-12-17       Impact factor: 6.005

7.  Rhodium(III)-catalyzed arene and alkene C-H bond functionalization leading to indoles and pyrroles.

Authors:  David R Stuart; Pamela Alsabeh; Michelle Kuhn; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2010-12-06       Impact factor: 15.419

8.  The vinyl moiety as a handle for regiocontrol in the preparation of unsymmetrical 2,3-aliphatic-substituted indoles and pyrroles.

Authors:  Malcolm P Huestis; Lina Chan; David R Stuart; Keith Fagnou
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

9.  Substituted pyrroles via olefin cross-metathesis.

Authors:  Timothy J Donohoe; Nicholas J Race; John F Bower; Cedric K A Callens
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

10.  Catalytic alkylation of methyl-N-heteroaromatics with alcohols.

Authors:  Benoît Blank; Rhett Kempe
Journal:  J Am Chem Soc       Date:  2010-01-27       Impact factor: 15.419

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  19 in total

1.  A mild and efficient AgSbF6-catalyzed synthesis of fully substituted pyrroles through a sequential propargylation/amination/cycloisomerization reaction.

Authors:  Satheesh Gujarathi; Xingui Liu; Lin Song; Howard Hendrickson; Guangrong Zheng
Journal:  Tetrahedron       Date:  2014-08-26       Impact factor: 2.457

2.  Catalytic acceptorless dehydrogenations: Ru-Macho catalyzed construction of amides and imines.

Authors:  Nathan J Oldenhuis; Vy M Dong; Zhibin Guan
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

3.  Ruthenium-Catalyzed Amination of Secondary Alcohols using Borrowing Hydrogen Methodology.

Authors:  Kostiantyn O Marichev; James M Takacs
Journal:  ACS Catal       Date:  2016-02-23       Impact factor: 13.084

Review 4.  Synthesis of N-Heterocycles via Oxidant-Free Dehydrocyclization of Alcohols Using Heterogeneous Catalysts.

Authors:  Kangkang Sun; Hongbin Shan; Guo-Ping Lu; Chun Cai; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-03       Impact factor: 16.823

5.  Ribose conversion with amino acids into pyrraline platform chemicals - expeditious synthesis of diverse pyrrole-fused alkaloid compounds.

Authors:  Soohyeon Cho; Lina Gu; Ik Joon In; Bo Wu; Taehoon Lee; Hakwon Kim; Sangho Koo
Journal:  RSC Adv       Date:  2021-09-23       Impact factor: 4.036

6.  Single-catalyst high-weight% hydrogen storage in an N-heterocycle synthesized from lignin hydrogenolysis products and ammonia.

Authors:  Daniel Forberg; Tobias Schwob; Muhammad Zaheer; Martin Friedrich; Nobuyoshi Miyajima; Rhett Kempe
Journal:  Nat Commun       Date:  2016-10-20       Impact factor: 14.919

7.  Direct Synthesis of Highly Substituted Pyrroles and Dihydropyrroles Using Linear Selective Hydroacylation Reactions.

Authors:  Manjeet K Majhail; Paul M Ylioja; Michael C Willis
Journal:  Chemistry       Date:  2016-04-23       Impact factor: 5.236

8.  Crystal structure and synthesis of 3-(1H-pyrrol-2-yl)-1-(thio-phen-2-yl)propanone.

Authors:  Dáire Gibbons; Ganapathi Emandi; Mathias O Senge
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2018-09-21

9.  Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds: modular and regiocontrolled synthesis of multisubstituted pyrroles.

Authors:  Wei Wen Tan; Naohiko Yoshikai
Journal:  Chem Sci       Date:  2015-08-03       Impact factor: 9.825

10.  Catalytic condensation for the formation of polycyclic heteroaromatic compounds.

Authors:  Daniel Forberg; Tobias Schwob; Rhett Kempe
Journal:  Nat Commun       Date:  2018-05-01       Impact factor: 14.919

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