Literature DB >> 25341623

Aerobic C-H olefination of indoles via a cross-dehydrogenative coupling in continuous flow.

Hannes P L Gemoets1, Volker Hessel, Timothy Noël.   

Abstract

Herein, we report the first site-selective, Pd(II)-catalyzed, cross-dehydrogenative Heck reaction of indoles in micro flow. By use of a capillary microreactor, we were able to boost the intrinsic kinetics to accelerate former hour-scale reaction conditions in batch to the minute range in flow. The synergistic use of microreactor technology and oxygen, as both terminal oxidant and mixing motif, highlights the sustainable aspect of this process.

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Year:  2014        PMID: 25341623     DOI: 10.1021/ol502910e

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

1.  Continuous-Flow Synthesis and Derivatization of Aziridines through Palladium-Catalyzed C(sp(3) )-H Activation.

Authors:  Jacek Zakrzewski; Adam P Smalley; Mikhail A Kabeshov; Matthew J Gaunt; Alexei A Lapkin
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-15       Impact factor: 15.336

2.  A Modular Flow Design for the meta-Selective C-H Arylation of Anilines.

Authors:  Hannes P L Gemoets; Gabriele Laudadio; Kirsten Verstraete; Volker Hessel; Timothy Noël
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-22       Impact factor: 15.336

3.  Mild and selective base-free C-H arylation of heteroarenes: experiment and computation.

Authors:  Hannes P L Gemoets; Indrek Kalvet; Alexander V Nyuchev; Nico Erdmann; Volker Hessel; Franziska Schoenebeck; Timothy Noël
Journal:  Chem Sci       Date:  2016-09-05       Impact factor: 9.825

Review 4.  The Use of Molecular Oxygen for Liquid Phase Aerobic Oxidations in Continuous Flow.

Authors:  Christopher A Hone; C Oliver Kappe
Journal:  Top Curr Chem (Cham)       Date:  2018-12-11

5.  Visible-Light-Promoted Iron-Catalyzed C(sp2 )-C(sp3 ) Kumada Cross-Coupling in Flow.

Authors:  Xiao-Jing Wei; Irini Abdiaj; Carlo Sambiagio; Chenfei Li; Eli Zysman-Colman; Jesús Alcázar; Timothy Noël
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-11       Impact factor: 15.336

6.  Selectivity, Speciation, and Substrate Control in the Gold-Catalyzed Coupling of Indoles and Alkynes.

Authors:  Ryan G Epton; William P Unsworth; Jason M Lynam
Journal:  Organometallics       Date:  2022-02-10       Impact factor: 3.876

7.  Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step.

Authors:  Yu-Jie Wang; Chen-Hui Yuan; De-Zhao Chu; Lei Jiao
Journal:  Chem Sci       Date:  2020-09-23       Impact factor: 9.825

8.  A flow reactor setup for photochemistry of biphasic gas/liquid reactions.

Authors:  Josef Schachtner; Patrick Bayer; Axel Jacobi von Wangelin
Journal:  Beilstein J Org Chem       Date:  2016-08-11       Impact factor: 2.883

9.  Homogeneous and Gas-Liquid Catellani-Type Reaction Enabled by Continuous-Flow Chemistry.

Authors:  Alessandra Casnati; Hannes P L Gemoets; Elena Motti; Nicola Della Ca'; Timothy Noël
Journal:  Chemistry       Date:  2018-08-28       Impact factor: 5.236

10.  Synthesis of 3-alkenylindoles through regioselective C-H alkenylation of indoles by a ruthenium nanocatalyst.

Authors:  Abhijit Paul; Debnath Chatterjee; Srirupa Banerjee; Somnath Yadav
Journal:  Beilstein J Org Chem       Date:  2020-01-29       Impact factor: 2.883

  10 in total

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