Angewandte Chemie - International Edition, volume 61, issue 17

Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction.

Burykina Julia V. ¹

Kobelev Andrey D ^{1, 2}

Shlapakov Nikita S ^{1, 3}

Kostyukovich Alexander Yu ¹

Fakhrutdinov Artem N. ¹

König Burkhard ³

Ananikov Valentine P. ^{1, 2}

Hide authors affiliations Show authors affiliations: 3 affiliations

Zelinsky Institute of Organic Chemistry Russian Academy of Sciences Leninsky Prospect, 47 Moscow 119991 Russia |

Lomonosov Moscow State University Leninskie Gory GSP-1, 1-3 Moscow 119991 Russia |

Institut für Organische Chemie Universität Regensburg Universitätstrasse 31 93053 Regensburg Germany |

Publication type: Journal Article

Publication date: 2022-03-02

Wiley

Journal: Angewandte Chemie - International Edition

Quartile SCImago

Quartile WOS

Impact factor: 16.6

ISSN: 14337851, 15213773

DOI: 10.1002/anie.202116888

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General Chemistry

Catalysis

Abstract

The first example of an intermolecular thiol–yne–ene coupling reaction is reported for the one‐pot construction of C−S and C−C bonds. Thiol–yne–ene coupling opens a new dimension in building molecular complexity to access densely functionalized products. The employment of Eosin Y/DBU/MeOH photocatalytic system suppresses hydrogen atom transfer (HAT) and associative reductant upconversion (via C−S three‐electron σ‐bond formation). Investigation of the reaction mechanism by combining online ESI‐UHRMS, EPR spectroscopy, isotope labeling, determination of quantum yield, cyclic voltammetry, Stern–Volmer measurements and computational modeling revealed a unique photoredox cycle with four radical‐involving stages. As a result, previously unavailable products of the thiol–yne–ene reaction were obtained in good yields with high selectivity. They can serve as stable precursors for synthesizing synthetically demanding activated 1,3‐dienes.

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Citations by journals

	1 2
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 2, 8% Organic Chemistry Frontiers 2 publications, 8%
Chemical Science	Chemical Science, 2, 8% Chemical Science 2 publications, 8%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 2, 8% Advanced Synthesis and Catalysis 2 publications, 8%
Russian Journal of Organic Chemistry	Russian Journal of Organic Chemistry, 2, 8% Russian Journal of Organic Chemistry 2 publications, 8%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 2, 8% Angewandte Chemie - International Edition 2 publications, 8%
Angewandte Chemie	Angewandte Chemie, 2, 8% Angewandte Chemie 2 publications, 8%
Green Chemistry	Green Chemistry, 2, 8% Green Chemistry 2 publications, 8%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 1, 4% Organic and Biomolecular Chemistry 1 publication, 4%
European Polymer Journal	European Polymer Journal, 1, 4% European Polymer Journal 1 publication, 4%
ChemPhotoChem	ChemPhotoChem, 1, 4% ChemPhotoChem 1 publication, 4%
ChemCatChem	ChemCatChem, 1, 4% ChemCatChem 1 publication, 4%
Chemistry - A European Journal	Chemistry - A European Journal, 1, 4% Chemistry - A European Journal 1 publication, 4%
Organic Process Research and Development	Organic Process Research and Development, 1, 4% Organic Process Research and Development 1 publication, 4%
Molecules	Molecules, 1, 4% Molecules 1 publication, 4%
Science China Chemistry	Science China Chemistry, 1, 4% Science China Chemistry 1 publication, 4%
Journal of Organic Chemistry	Journal of Organic Chemistry, 1, 4% Journal of Organic Chemistry 1 publication, 4%
Chemical Communications	Chemical Communications, 1, 4% Chemical Communications 1 publication, 4%
Journal of the Taiwan Institute of Chemical Engineers	Journal of the Taiwan Institute of Chemical Engineers, 1, 4% Journal of the Taiwan Institute of Chemical Engineers 1 publication, 4%
	1 2

Citations by publishers

	1 2 3 4 5 6 7 8 9
Wiley	Wiley, 9, 36% Wiley 9 publications, 36%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 8, 32% Royal Society of Chemistry (RSC) 8 publications, 32%
American Chemical Society (ACS)	American Chemical Society (ACS), 2, 8% American Chemical Society (ACS) 2 publications, 8%
Pleiades Publishing	Pleiades Publishing, 2, 8% Pleiades Publishing 2 publications, 8%
Elsevier	Elsevier, 1, 4% Elsevier 1 publication, 4%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 4% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 4%
Springer Nature	Springer Nature, 1, 4% Springer Nature 1 publication, 4%
Taiwan Institute of Chemical Engineers	Taiwan Institute of Chemical Engineers, 1, 4% Taiwan Institute of Chemical Engineers 1 publication, 4%
	1 2 3 4 5 6 7 8 9

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Burykina J. V. et al. Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction. // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 17.

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Burykina J. V., Kobelev A. D., Shlapakov N. S., Kostyukovich A. Yu., Fakhrutdinov A. N., König B., Ananikov V. P. Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction. // Angewandte Chemie - International Edition. 2022. Vol. 61. No. 17.

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RIS Copy

TY - JOUR

DO - 10.1002/anie.202116888

UR - https://doi.org/10.1002%2Fanie.202116888

TI - Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction.

T2 - Angewandte Chemie - International Edition

AU - Fakhrutdinov, Artem N.

AU - Burykina, Julia V.

AU - Kobelev, Andrey D

AU - Shlapakov, Nikita S

AU - Kostyukovich, Alexander Yu

AU - König, Burkhard

AU - Ananikov, Valentine P.

PY - 2022

DA - 2022/03/02 00:00:00

PB - Wiley

IS - 17

VL - 61

SN - 1433-7851

SN - 1521-3773

ER -

BibTex

Cite this

BibTex Copy

@article{2022_Burykina,

author = {Artem N. Fakhrutdinov and Julia V. Burykina and Andrey D Kobelev and Nikita S Shlapakov and Alexander Yu Kostyukovich and Burkhard König and Valentine P. Ananikov},

title = {Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-yne-ene Coupling Reaction.},

journal = {Angewandte Chemie - International Edition},

year = {2022},

volume = {61},

publisher = {Wiley},

month = {mar},

url = {https://doi.org/10.1002%2Fanie.202116888},

number = {17},

doi = {10.1002/anie.202116888}

}

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Publisher

Wiley

Journal

Angewandte Chemie - International Edition

Quartile SCImago

Quartile WOS

Impact factor

16.6

ISSN

14337851 (Print)
15213773 (Electronic)

Labs

Laboratory of metal-complex and nanoscale catalysts

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