Oxidative [4+2] Annulation of Styrenes with Alkynes Under External-oxidant-free Conditions

Overview

Journal Nat Commun

Specialty Biology

Date 2018 Mar 28

PMID 29581484

Citations 9

Authors

Guoting Zhang

Yulin Lin

Xu Luo

Xia Hu

Cong Chen

Aiwen Lei

Affiliations

Soon will be listed here.

Abstract

The sequenced Diels-Alder/oxidation reaction represents a powerful route for the construction of aromatic compounds in organic synthesis. The oxidative Diels-Alder reaction with H evolution would be a more ideal approach that can avoid the additional oxidation procedure and stoichiometric oxidant. Herein, an oxidative [4 + 2] annulation reaction of styrene derivatives with electron-rich dienophiles accompanying the H generation has been developed by using the synergistic merger of photoredox and cobaloxime catalyst. With respect to atom and step-economy ideals, this dual catalytic system enables the formation of high-value molecules from feedstock chemicals in a single step under room temperature.

Citing Articles

Sustainable tandem acylation/Diels-Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents.

Yildirim A Beilstein J Org Chem. 2024; 20:1308-1319.

PMID: 38887569 PMC: 11181201. DOI: 10.3762/bjoc.20.114.

Visible Light-Promoted Regioselective Benzannulation of Vinyl Sulfoxonium Ylides with Ynoates.

Davas D, Gopalakrishnan D, Kumar S, Anmol , Karmakar T, Vaitla J JACS Au. 2024; 4(3):1073-1080.

PMID: 38559716 PMC: 10976606. DOI: 10.1021/jacsau.3c00802.

Applications of Vanadium, Niobium, and Tantalum Complexes in Organic and Inorganic Synthesis.

Xu X, Wang H, Tan C, Ye X ACS Org Inorg Au. 2023; 3(2):74-91.

PMID: 37035284 PMC: 10080730. DOI: 10.1021/acsorginorgau.2c00056.

Hydrogen-Atom-Transfer-Initiated Radical/Polar Crossover Annulation Cascade for Expedient Access to Complex Tetralins.

Johnson L, Barnes G, Fernandez S, Vanderwal C Angew Chem Int Ed Engl. 2023; 62(21):e202303228.

PMID: 36952637 PMC: 10164078. DOI: 10.1002/anie.202303228.

Photocatalytic Hydroalkylation of Aryl-Alkenes.

Buettner C, Schnurch M, Bica-Schroder K J Org Chem. 2022; 87(16):11042-11047.

PMID: 35914236 PMC: 9396655. DOI: 10.1021/acs.joc.2c01304.

References

Dempsey J, Brunschwig B, Winkler J, Gray H . Hydrogen evolution catalyzed by cobaloximes. Acc Chem Res. 2009; 42(12):1995-2004. DOI: 10.1021/ar900253e. View

Artero V, Chavarot-Kerlidou M, Fontecave M . Splitting water with cobalt. Angew Chem Int Ed Engl. 2011; 50(32):7238-66. DOI: 10.1002/anie.201007987. View

Du P, Schneider J, Luo G, Brennessel W, Eisenberg R . Visible light-driven hydrogen production from aqueous protons catalyzed by molecular cobaloxime catalysts. Inorg Chem. 2009; 48(11):4952-62. DOI: 10.1021/ic900389z. View

Prier C, Rankic D, MacMillan D . Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem Rev. 2013; 113(7):5322-63. PMC: 4028850. DOI: 10.1021/cr300503r. View

Stang E, White M . Molecular complexity via C-H activation: a dehydrogenative Diels-Alder reaction. J Am Chem Soc. 2011; 133(38):14892-5. PMC: 3292869. DOI: 10.1021/ja2059704. View

Fukuzumi S, Kotani H, Ohkubo K, Ogo S, Tkachenko N, Lemmetyinen H . Electron-transfer state of 9-mesityl-10-methylacridinium ion with a much longer lifetime and higher energy than that of the natural photosynthetic reaction center. J Am Chem Soc. 2004; 126(6):1600-1. DOI: 10.1021/ja038656q. View

Trost B . The atom economy--a search for synthetic efficiency. Science. 1991; 254(5037):1471-7. DOI: 10.1126/science.1962206. View

Hamilton D, Nicewicz D . Direct catalytic anti-markovnikov hydroetherification of alkenols. J Am Chem Soc. 2012; 134(45):18577-80. PMC: 3513336. DOI: 10.1021/ja309635w. View

Corey E . Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications. Angew Chem Int Ed Engl. 2009; 41(10):1650-67. DOI: 10.1002/1521-3773(20020517)41:10<1650::aid-anie1650>3.0.co;2-b. View

10.

Romero N, Nicewicz D . Organic Photoredox Catalysis. Chem Rev. 2016; 116(17):10075-166. DOI: 10.1021/acs.chemrev.6b00057. View

11.

Wang T, Naredla R, Thompson S, Hoye T . The pentadehydro-Diels-Alder reaction. Nature. 2016; 532(7600):484-8. PMC: 4877333. DOI: 10.1038/nature17429. View

12.

Lin S, Ischay M, Fry C, Yoon T . Radical cation Diels-Alder cycloadditions by visible light photocatalysis. J Am Chem Soc. 2011; 133(48):19350-3. PMC: 3227774. DOI: 10.1021/ja2093579. View

13.

Narayanam J, Stephenson C . Visible light photoredox catalysis: applications in organic synthesis. Chem Soc Rev. 2010; 40(1):102-13. DOI: 10.1039/b913880n. View

14.

Kocsis L, Kagalwala H, Mutto S, Godugu B, Bernhard S, Tantillo D . Mechanistic Insight into the Dehydro-Diels-Alder Reaction of Styrene-Ynes. J Org Chem. 2015; 80(23):11686-98. DOI: 10.1021/acs.joc.5b00200. View

15.

Wessig P, Muller G . The dehydro-Diels-Alder reaction. Chem Rev. 2008; 108(6):2051-63. DOI: 10.1021/cr0783986. View

16.

Levin M, Kim S, Toste F . Photoredox Catalysis Unlocks Single-Electron Elementary Steps in Transition Metal Catalyzed Cross-Coupling. ACS Cent Sci. 2016; 2(5):293-301. PMC: 4882737. DOI: 10.1021/acscentsci.6b00090. View

17.

Hoye T, Baire B, Niu D, Willoughby P, Woods B . The hexadehydro-Diels-Alder reaction. Nature. 2012; 490(7419):208-12. PMC: 3538845. DOI: 10.1038/nature11518. View

18.

Skubi K, Blum T, Yoon T . Dual Catalysis Strategies in Photochemical Synthesis. Chem Rev. 2016; 116(17):10035-74. PMC: 5083252. DOI: 10.1021/acs.chemrev.6b00018. View

19.

Yoon T, Ischay M, Du J . Visible light photocatalysis as a greener approach to photochemical synthesis. Nat Chem. 2010; 2(7):527-32. DOI: 10.1038/nchem.687. View

20.

Aragones A, Haworth N, Darwish N, Ciampi S, Mannix E, Wallace G . Electrostatic catalysis of a Diels-Alder reaction. Nature. 2016; 531(7592):88-91. DOI: 10.1038/nature16989. View