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Acetonitrile Activation: An Effective Two-Carbon Unit For Cyclization.

Qixue Qin, Xiao Luo, Jialiang Wei, Yuchao Zhu, X. Wen, Song Song, Ning Jiao
Published 2019 · Medicine, Chemistry
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A novel activation of acetonitrile for the construction of cyclobutenones by [2+2] cyclization was developed. Acetonitrile is utilized for the first time as two-carbon (C2) cyclization building block. The present protocol successfully inhibits the competitive cycloaddition with the C≡N bond of acetonitrile, but enables the in situ formation of an unsaturated carbon-carbon bond and the subsequent cycloaddition as a C2 unit. This chemistry features simple reaction conditions, high chemoselectivities, wide substrate scope, and offers a new and practical approach to cyclobutenones and cyclobuteneimines.
This paper references
10.1002/anie.198807971
Cyclobutanones and Cyclobutenones in Nature and in Synthesis [New Synthetic Methods(71)]
Daniel Belluŝ (1988)
10.1126/science.aat6205
Tandem catalysis for asymmetric coupling of ethylene and enynes to functionalized cyclobutanes
Vinayak Vishnu Pagar (2018)
10.1002/anie.201303916
Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.
Vaneet Saini (2013)
10.1002/anie.201204098
Direct transformation of secondary amides into secondary amines: triflic anhydride activated reductive alkylation.
Kaijiong Xiao (2012)
10.1002/anie.201106112
Iron-catalyzed C-H and C-C bond cleavage: a direct approach to amides from simple hydrocarbons.
Chong Qin (2011)
10.1246/cl.2005.1462
Ruthenium-catalyzed Reconstructive Synthesis of Functional Organic Molecules via Cleavage of Carbon–Carbon Bonds
Teruyuki Kondo (2005)
10.1021/ja0508931
A nickel-catalyzed route to pyridines.
Michael M McCormick (2005)
10.1002/tcr.201700017
Cascades of Interrupted Pummerer Reaction-Sigmatropic Rearrangement.
Hideki Yorimitsu (2017)
10.1002/anie.201511002
Cationic Cobalt(III) Catalyzed Indole Synthesis: The Regioselective Intermolecular Cyclization of N-Nitrosoanilines and Alkynes.
Yujie Liang (2016)
10.1021/ja00219a073
Cycloaddition reactions of silyloxyacetylenes with ketenes: synthesis of cyclobutenones, resorcinols, and .DELTA.-6-tetrahydrocannabinol
Conrad J. Kowalski (1988)
10.1039/C39900001603
Light-mediated cyanomethylation of cycloalkenes with acetonitrile
Harikisan R. Sonawane (1990)
10.1021/jacs.7b02983
Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides.
Aurélien de la Torre (2017)
10.1021/acs.chemrev.5b00138
Catalytic C-C Bond Activations via Oxidative Addition to Transition Metals.
Laetitia Souillart (2015)
10.1021/ja0399066
Remarkably facile hexatriene electrocyclizations as a route to functionalized cyclohexenones via ring expansion of cyclobutenones.
Nabi A. Magomedov (2004)
10.1021/jo802193z
An efficient intramolecular 1,3-dipolar cycloaddition involving 2-(1,2-dichlorovinyloxy)aryldiazomethanes: a one-pot synthesis of benzofuropyrazoles from salicylaldehydes.
Zachary S. Sales (2009)
10.1021/ar50109a001
Transition-metal-catalyzed acetylene cyclizations in organic synthesis
K. Peter C. Vollhardt (1977)
10.1002/anie.201300586
Copper(II)-catalyzed three-component cascade annulation of diaryliodoniums, nitriles, and alkynes: a regioselective synthesis of multiply substituted quinolines.
Yong Wang (2013)
10.1038/364676a0
The fall of the C-C bond
William D Jones (1993)
10.1021/ja2029188
An efficient [2 + 2 + 1] synthesis of 2,5-disubstituted oxazoles via gold-catalyzed intermolecular alkyne oxidation.
Weimin He (2011)
10.1038/ncomms14720
Oxidative 1,2-carboamination of alkenes with alkyl nitriles and amines toward γ-amino alkyl nitriles
Yanyun Liu (2017)
10.1002/anie.201102001
A simple and highly efficient iron catalyst for a [2+2+2] cycloaddition to form pyridines.
Chunxiang Wang (2011)
10.1021/ACSCATAL.7B03334
Recent Advances in Radical-Initiated C(sp3)–H Bond Oxidative Functionalization of Alkyl Nitriles
Xue-Qiang Chu (2018)
10.1021/jacs.7b00969
Redox-Neutral α-Arylation of Alkyl Nitriles with Aryl Sulfoxides: A Rapid Electrophilic Rearrangement.
Li Shang (2017)
10.1002/ANGE.201303916
Übergangsmetallkatalysierte C‐C‐Kupplungen mit Ethylen im Labormaßstab
Vaneet Saini (2013)
10.1021/ja01192a022
A new reaction of nitriles; amides from alkenes and mononitriles.
John J. Ritter (1948)
10.1038/s41467-018-03246-4
Cobalt-catalyzed electrooxidative C-H/N-H [4+2] annulation with ethylene or ethyne
Shan Tang (2018)
10.1021/ja00390a054
A [4 + 4] annulation approach to eight-membered carbocyclic compounds
Rick L Danheiser (1982)
10.1002/(SICI)1521-3757(19990401)111:7<918::AID-ANGE918>3.0.CO;2-X
Metallinsertion in C‐C‐Bindungen in Lösung
Boris Rybtchinski (1999)
10.1002/anie.200503776
Straightforward one-pot synthesis of trifluoromethyl sulfonium salts.
Emmanuel Magnier (2006)
10.1002/ange.19810931035
Cyclobutanon‐ und Cyclobutenon‐Derivate durch Reaktion tertiärer Amide mit Alkenen bzw. Alkinen
Jean‐Bernard Falmagne (1981)
10.1021/jo070222g
Chiral polycyclic ketones via desymmetrization of dihaloolefins.
Giuseppe Borsato (2007)
10.1002/anie.201705353
Copper-Catalyzed Three-Component Carboazidation of Alkenes with Acetonitrile and Sodium Azide.
Ala Bunescu (2017)
10.1021/ja00510a022
Preparation and characterization of tantalum(III) olefin complexes and tantalum(V) metallacyclopentane complexes made from acyclic .alpha. olefins
Stephan James Mclain (1979)
10.1002/ANGE.201307051
Die photoredoxkatalysierte Meerwein-Addition: intermolekulare Aminoarylierung von Alkenen†
Durga Prasad Hari (2014)
10.1002/ange.19881000607
Cyclobutanone und Cyclobutenone in der Natur und in der Synthese
Daniel Belluŝ (1988)
10.1021/ja00402a076
Silver(I) photocatalyzed addition of acetonitrile to norbornene
Joseph W. Bruno (1981)
10.1002/(SICI)1521-3773(19990401)38:7<870::AID-ANIE870>3.0.CO;2-3
Metal Insertion into C-C Bonds in Solution.
Boris Rybtchinski (1999)
10.1055/S-0032-1316850
Recent Advances in the Synthesis and Application of Benzocyclobutenones and Related Compounds
Areli Flores-Gaspar (2013)
10.1016/S0040-4020(00)00093-4
Chemical transformations induced by triflic anhydride
Ivan L. Baraznenok (2000)
10.1021/jacs.6b04061
Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides
Veronica Tona (2016)
10.1021/JACS.6B08094
Direct Tryptophols Synthesis from 2-Vinylanilines and Alkynes via C≡C Triple Bond Cleavage and Dioxygen Activation.
Tao Shen (2016)
10.1021/ja105194s
Controlled and chemoselective reduction of secondary amides.
Guillaume Pelletier (2010)
10.1016/S0022-1139(00)00250-5
Cycloaddition reactions of furan derivatives with trifluoroethene
Richard D. Chambers (2000)
10.1021/acs.joc.6b00675
Making the Least Reactive Electrophile the First in Class: Domino Electrophilic Activation of Amides.
Daniel Kaiser (2016)
10.1021/acs.orglett.7b01145
Photoredox-Catalyzed Diamidation and Oxidative Amidation of Alkenes: Solvent-Enabled Synthesis of 1,2-Diamides and α-Amino Ketones.
Qixue Qin (2017)
10.1021/ja060626a
Synthesis of substituted pyridine derivatives via the ruthenium-catalyzed cycloisomerization of 3-azadienynes.
Mohammad Movassaghi (2006)
10.1002/anie.198108791
Cyclobutanone and Cyclobutenone Derivatives By Reaction of Tertiary Amides With Alkenes Or Alkynes
Jean‐Bernard Falmagne (1981)
10.1016/S0040-4039(01)91114-1
Vicinal alkylation of alkynes. A short route toward Δα,β butenolides, furans and cyclopentenones.
C. Schmit (1984)
10.1016/J.TETLET.2016.04.092
Synthesis of amino-cyclobutanes via [2 + 2] cycloadditions involving keteniminium intermediates
Amandine Kolleth (2016)
10.1002/anie.201705859
Transforming Olefins into γ,δ-Unsaturated Nitriles through Copper Catalysis.
Xuesong Wu (2017)
10.1038/nchem.1268
Chemoselective synthesis of ketones and ketimines by addition of organometallic reagents to secondary amides.
William S. Bechara (2012)
10.1002/chem.201603382
Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis.
Peng-hao Chen (2016)
10.1021/ja073912a
Direct synthesis of pyridine derivatives.
Mohammad Movassaghi (2007)
10.1039/B607877J
The fascinating construction of pyridine ring systems by transition metal-catalysed [2 + 2 + 2] cycloaddition reactions.
Bárbara Heller (2007)
10.1002/anie.201206382
Synthesis of oxazoles through copper-mediated aerobic oxidative dehydrogenative annulation and oxygenation of aldehydes and amines.
Zejun Xu (2012)
10.1002/anie.201802082
Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates.
Hai Huang (2018)
10.1021/jacs.5b05843
Rh-Catalyzed Construction of Quinolin-2(1H)-ones via C-H Bond Activation of Simple Anilines with CO and Alkynes.
Xinyao Li (2015)
10.1021/cr400628s
Recent advances in transition-metal-catalyzed functionalization of unstrained carbon-carbon bonds.
Feng Chen (2014)
10.1021/ja3028394
Iridium-catalyzed [2 + 2 + 2] cycloaddition of α,ω-diynes with nitriles.
Gen Onodera (2012)
10.1002/anie.201307051
The photoredox-catalyzed Meerwein addition reaction: intermolecular amino-arylation of alkenes.
Durga Prasad Hari (2014)
10.1016/J.CHEMPR.2018.03.008
Chemoselective Nitrosylation of Anilines and Alkynes via Fragmentary or Complete NO Incorporation
Jun Qing Pan (2018)
10.1021/cr300100s
Synthesis of heterocycles via palladium-catalyzed carbonylations.
Xiao-Feng Wu (2013)
10.1021/jacs.7b02977
Metal-Free Electrophilic Phosphination/Cyclization of Alkynes.
Yuto Unoh (2017)
10.1021/jacs.6b08662
Selective Functionalization of Pyridines via Heterocyclic Phosphonium Salts.
Michael C Hilton (2016)
10.1021/ja212020b
Intermolecular Ritter-type C-H amination of unactivated sp3 carbons.
Quentin Michaudel (2012)
10.1021/cr030677f
Construction of pyridine rings by metal-mediated [2 + 2 + 2] cycloaddition.
Jesús A Varela (2003)
10.1039/c6ob00091f
Trihaloethenes as versatile building blocks for organic synthesis.
Adriana S. Grossmann (2016)
10.1021/jacs.5b12579
Metal-Free CH-CH-Type Cross-Coupling of Arenes and Alkynes Directed by a Multifunctional Sulfoxide Group.
José A Fernández-Salas (2016)
10.1002/anie.201603889
Metal-Free [2+2+2] Cycloaddition of Ynamides and Nitriles: Mild and Regioselective Synthesis of Fully Substituted Pyridines.
Yong Wang (2016)
10.1021/ja993314z
[2 + 2] Cycloreversion of [4.3.2]Propella-1,3,11-trienes: An Approach to Cyclo[n]carbons from Propellane-Annelated Dehydro[n]annulenes
Yoshito Tobe (2000)
10.1002/anie.201105505
Implanting nitrogen into hydrocarbon molecules through C-H and C-C bond cleavages: a direct approach to tetrazoles.
Feng Chen (2011)
10.1021/ja01192a023
A new reaction of nitriles; synthesis of t-carbinamines.
John J. Ritter (1948)
10.1039/c1cs15029d
Recent advances in [2+2+2] cycloaddition reactions.
Gema Domínguez (2011)



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