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A. Thakur, J. Louie (2015)
‘Advances in Nickel-Catalyzed Cycloaddition Reactions to Construct Carbocycles and Heterocycles’, 48
D. Holte, D. C. G. Götz, P. S. Baran (2012)
‘An Approach to Mimicking the Sesquiterpene Cyclase Phase by Nickel-Promoted Diene/Alkyne Cooligomerization’, 77
S. Chakraborty, P. Bhattacharya, H. Dai, H. Guan (2015)
‘Nickel and Iron Pincer Complexes as Catalysts for the Reduction of Carbonyl Compounds’, 48
M. Tamizmani, C. Sivasankar (2017)
‘Synthesis, characterization and catalytic application of some novel PNP−Ni(II) complexes: Regio-selective [2+2+2] cycloaddition reaction of alkyne’, 845
D. Brenna, M. Villa, T. N. Gieshoff, F. Fischer, M. Hapke, A. J. Wangelin (2017)
‘Iron-Catalyzed Cyclotrimerization of Terminal Alkynes by Dual Catalyst Activation in the Absence of Reductants’, 56
Y. Kenta, M. Ichiro, M. Koichi, T. Hideo (2007)
‘RhCl3/Amine-catalyzed Cyclotrimerization of Alkynes’, 36
Y. Segawa, M. Kuwayama, Y. Hijikata, M. Fushimi, T. Nishihara, J. Pirillo, J. Shirasaki, N. Kubota, K. Itami (2019)
‘Topological molecular nanocarbons: All-benzene catenane and trefoil knot’, 365
J.-P. Zhao, S.-C. Chan, C.-Y. Ho (2015)
‘Substituted 1,3-cyclohexadiene synthesis by NHC−Nickel(0) catalyzed [2+2+2] cycloaddition of 1, n-Enyne’, 71
Y. Liu, J. Cornella, R. Martin (2014)
‘Ni-Catalyzed Carboxylation of Unactivated Primary Alkyl Bromides and Sulfonates with CO2’, 136
P. Tagliatesta, B. Floris, P. Galloni, A. Leoni, G. D'Arcangelo (2003)
‘The First Solvent-Free Cyclotrimerization Reaction of Arylethynes Catalyzed by Rhodium Porphyrins’, 42
D. Wang, T. Xu (2021)
‘A Pivotal Role of Chloride Ion on Nickel-Catalyzed Enantioselective Reductive Cross-Coupling to Perfluoroalkylated Boronate Esters’, 11
M. G. McKee, G. L. Wilkes, R. H. Colby, T. E. Long (2004)
‘Correlations of Solution Rheology with Electrospun Fiber Formation of Linear and Branched Polyesters’, 37
G. Domínguez, J. Pérez-Castells (2011)
‘Recent advances in [2+2+2] cycloaddition reactions’, 40
K. Tanaka, K. Shirasaka (2003)
‘Highly Chemo- and Regioselective Intermolecular Cyclotrimerization of Alkynes Catalyzed by Cationic Rhodium(I)/Modified BINAP Complexes’, 5
Z. Sun, E. Yue, M. Qu, I. V. Oleynik, I. I. Oleynik, K. Li, T. Liang, W. Zhang, W.-H. Sun (2015)
‘8-(2-Cycloalkylphenylimino)-5,6,7-trihydro-quinolylnickel halides: Polymerizing ethylene to highly branched and lower molecular weight polyethylenes’, 2
S. T. Heller, S. R. Natarajan (2007)
‘Rapid Access to Pyrazolo[3,4-C]pyridines via Alkyne Annulation: Limitations of Steric Control in Nickel-Catalyzed Alkyne Insertions’, 9
X. Tang, Z. Wang, Y. Li, H. Yan (2013)
‘Reactivity of the 16-electron CpCo half-sandwich complex containing a B(3,6)-disubstituted o-carborane-1,2-dithiolate ligand’, 747
T.-C. Wu, J.-J. Chen, Y.-T. Wu (2011)
‘Nickel-Catalyzed Tetramerization of Alkynes: Synthesis and Structure of Octatetraenes’, 13
C.-S. Wang, Q. Sun, F. García, C. Wang, N. Yoshikai (2021)
‘Robust Cobalt Catalyst for Nitrile/Alkyne [2+2+2] Cycloaddition: Synthesis of Polyarylpyridines and Their Mechanochemical Cyclodehydrogenation to Nitrogen-Containing Polyaromatics’, 60
S. Nishigaki, Y. Shibata, K. Tanaka (2017)
‘Rhodium-Catalyzed Chemo-and Regioselective Intermolecular Cross-Cyclotrimerization of Nonactivated Terminal and Internal Alkynes’, 82
S. K. Rodrigo, H. Guan (2012)
‘Quick Installation of a 1,4-Difunctionality via Regioselective Nickel-Catalyzed Reductive Coupling of Ynoates and Aldehydes’, 77
B. H. Lipshutz, J. A. Sclafani, P. A. Blomgren (2000)
‘Biaryls via Suzuki Cross-Couplings Catalyzed by Nickel on Charcoal’, 56
J.-S. Yang, H.-H. Huang, S.-H. Lin (2009)
‘Facile Multistep Synthesis of Isotruxene and Isotruxenone’, 74
M. Fabbian, N. Marsich, E. Farnetti (2004)
‘Organoiridium compounds with bidentate phosphines as highly regioselective catalysts for alkynes cyclotrimerization’, 357
Z. Nairoukh, M. Fanun, M. Schwarze, R. Schomäcker, J. Blum (2014)
‘Cyclotrimerization of alkynes vs. ketone formation in aqueous microemulsion’, 382
D. Eisenberg, R. Shenhar, M. Rabinovitz (2010)
‘Synthetic approaches to aromatic belts: building up strain in macrocyclic polyarenes’, 39
A. Ciammaichella, A. Leoni, P. Tagliatesta (2010)
‘Ruthenium porphyrin bound to a Merrifield resin as heterogeneous catalyst for the cyclooligomerization of arylethynes’, 34
S. Pal, C. Uyeda (2015)
‘Evaluating the Effect of Catalyst Nuclearity in Ni-Catalyzed Alkyne Cyclotrimerizations’, 137
I. Czeluśniak, P. Kocięcka, T. Szymańska-Buzar (2012)
‘The effect of the oxidation state of molybdenum complexes on the catalytic transformation of terminal alkynes: Cyclotrimerization vs. polymerization’, 716
H. Miura, Y. Tanaka, K. Nakahara, Y. Hachiya, K. Endo, T. Shishido (2018)
‘Concerted Catalysis by Adjacent Palladium and Gold in Alloy Nanoparticles for the Versatile and Practical [2+2+2] Cycloaddition of Alkynes’, 57
P. Mauret, P. Alphonse (1984)
‘Etude du mecanisme de la cyclotrimerisation catalytique de l′hexyne-3 par l′intermediaire d′un complexe cyclobutadienique du nickel’, 276
G. F. P. Souza, A. G. Salles (2019)
‘Persulfate-mediated synthesis of polyfunctionalized benzenes in water via the benzannulation of alkynes and α,β-unsaturated compounds’, 21
N. Yoshikai, H. Mashima, E. Nakamura (2005)
‘Nickel-Catalyzed Cross-Coupling Reaction of Aryl Fluorides and Chlorides with Grignard Reagents under Nickel/Magnesium Bimetallic Cooperation’, 127
A. Mantovani, A. Marcomini, U. Belluco (1985)
‘Selective oligomerization of phenylacetylene to 1,2,4-triphenylbenzene catalyzed by Ni(CO)3(P(O-i-C3H7)3’, 30
A. K. Jhingan, W. F. Maier (1987)
‘Homogeneous catalysis with a heterogeneous palladium catalyst. An effective method for the cyclotrimerization of alkynes’, 52
J. Gao, C. Liu, Z. Li, H. Liang, Y. Ao, J. Zhao, Y. Wang, Y. Wu, Y. Liu (2020)
‘Catalytic C−C Cleavage/Alkyne–Carbonyl Metathesis Sequence of Cyclobutanones’, 22
Z. Zhu, C. Wang, X. Xiang, C. Pi, X. Zhou (2006)
‘DyI2 initiated mild and highly selective silyl radical-catalyzed cyclotrimerization of terminal alkynes and polymerization of MMA’
O. V. Ozerov, B. O. Patrick, F. T. Ladipo (2000)
‘Highly Regioselective [2+2+ 2] Cycloaddition of Terminal Alkynes Catalyzed by η6-Arene Complexes of Titanium Supported by Dimethylsilyl-Bridged p-tert-Butyl Calix[4]arene Ligand’, 122
Y. Sato, T. Nishimata, M. Mori (1994)
‘Asymmetric Synthesis of Isoindoline and Isoquinoline Derivatives Using Nickel(0)-Catalyzed [2+2+2] Cocyclization’, 59
F. Montilla, T. Avilés, T. Casimiro, A. A. Ricardo, M. N. Ponte (2001)
‘CpCo(CO)2-catalysed cyclotrimerisation of alkynes in supercritical carbon dioxide’, 632
I. P. Beletskaya, A. V. Cheprakov (2000)
‘The Heck Reaction as a Sharpening Stone of Palladium Catalysis’, 100
V. Cadierno, J. Francos, S. E. García-Garrido, J. Gimeno (2011)
‘Ruthenium-catalyzed intermolecular [2+2+2] alkyne cyclotrimerization in aqueous media under microwave irradiation’, 4
N. Mori, S. Ikeda, Y. Sato (1999)
‘Selective Cyclotrimerization of Enones and Alkynes by a Nickel and Aluminum Catalytic System’, 121
C. Xi, Z. Sun, Y. Liu (2013)
‘Cyclotrimerization of terminal alkynes catalyzed by the system of NiCl2/Zn and (benzimidazolyl)-6-(1-(arylimino)ethyl)pyridines’, 42
K. Liang, L. Lu, X. Liu, D. Yang, S. Wang, Y. Gao, H. Alhumade, H. Yi, A. Lei (2021)
‘Electrochemical Cobalt-catalyzed Cyclotrimerization of Alkynes to 1,2,4-Substituted Arenes’, 11
W. Reppe, W. J. Schweckendiek (1948)
‘Cyclisierende Polymerisation von Acetylen. III Benzol, Benzolderivate und hydroaromatische Verbindungen’, 560
J. Louie, J. E. Gibby, M. V. Farnworth, T. N. Tekavec (2002)
‘Efficient Nickel-Catalyzed [2+2+2] Cycloaddition of CO2 and Diynes’, 124
Y. Yano, N. Mitoma, K. Matsushima, F. Wang, K. Matsui, A. Takakura, Y. Miyauchi, H. Ito, K. Itami (2019)
‘RETRACTED ARTICLE: Living annulative π-extension polymerization for graphene nanoribbon synthesis’, 571
A. Joosten, M. Soueidan, C. Denhez, D. Harakat, F. Hélion, J.-L. Namy, J.-L. Vasse, J. Szymoniak (2008)
‘Multimetallic Zirconocene-Based Catalysis: Alkyne Dimerization and Cyclotrimerization Reactions’, 27
J. Terao, H. Watabe, N. Kambe (2005)
‘Ni-Catalyzed Alkylative Dimerization of Vinyl Grignard Reagents Using Alkyl Fluorides’, 127
S. Karabulut, B. Sariaslan, B. Ö. Öztürk (2013)
‘A ruthenium-based catalytic system with switchable selectivity between cyclotrimerization and enyne metathesis/Diels–Alder reactions of terminal alkynes’, 41
J.-H. Li, Y.-X. Xie (2004)
‘Novel role of carbon dioxide as a selective agent in palladium-catalyzed cyclotrimerization of alkynes’, 22
P. Knochel, W. Dohle, N. Gommermann, F. F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu (2003)
‘Highly Functionalized Organomagnesium Reagents Prepared through Halogen–Metal Exchange’, 42
J. L. Arias, A. Cabrera, P. Sharma, N. Rosas, A. Toscano, E. E. Martínez, L. Rubio-Pérez (2009)
‘Competitive intermolecular cyclotrimerization and cyclocarbonylation products in Pauson–Khand reaction’, 10
S. K. Rodrigo, I. V. Powell, M. G. Coleman, J. A. Krause, H. Guan (2013)
‘Efficient and regioselective nickel-catalyzed [2+2+2] cyclotrimerization of ynoates and related alkynes’, 11
A. Jeevanandam, R. P. Korivi, I−W. Huang, C.-H. Cheng (2002)
‘Ni-Catalyzed Highly Regio- and Chemoselective Cocycloaddition of Nonconjugated Diynes with 1,3-Diynes: A Novel Method for Polysubstituted Arylalkynes’, 4
J. Yang, J. G. Verkade (1998)
‘Disilane-Catalyzed Cyclotrimerization of Acetylenes’, 120
G. L. O. Wilson, M. Abraha, J. A. Krause, H. Guan (2015)
‘Reactions of phenylacetylene with nickel POCOP-pincer hydride complexes resulting in different outcomes from their palladium analogues’, 44
J. M. Wood, E. N. Silva Júnior, J. F. Bower (2020)
‘Rh-Catalyzed [2+2+2] Cycloadditions with Benzoquinones: De Novo Access to Naphthoquinones for Lignan and Type II Polyketide Synthesis’, 22
K. Yang, P. Wang, Z.-Y. Sun, M. Guo, W. Zhao, X. Tang, G. Wang (2021)
‘Hydrogen-Bonding Controlled Nickel-Catalyzed Regioselective Cyclotrimerization of Terminal Alkynes’, 23
E. Elakkari, B. Floris, P. Galloni, P. Tagliatesta (2005)
‘The Formation of 1-Aryl-Substituted Naphthalenes by an Unusual Cyclization of Arylethynes Catalyzed by Ruthenium and Rhodium Porphyrins’
H. Chen, S. Sun, X. Liao (2019)
‘Nickel-Catalyzed Decarboxylative Alkenylation of Anhydrides with Vinyl Triflates or Halides’, 21
S. M. Weber, G. Hilt (2019)
‘Chemoselective Cobalt (I)-Catalyzed Cyclotrimerization of (Un)Symmetrical 1,3-Butadiynes for the Synthesis of 1,2,4-Regioisomers’, 21
N. Saino, F. Amemiya, E. Tanabe, K. Kase, S. Okamoto (2006)
‘A Highly Practical Instant Catalyst for Cyclotrimerization of Alkynes to Substituted Benzenes’, 8
X. Bu, Z. Zhang, X. Zhou (2010)
‘Switching from Dimerization to Cyclotrimerization Selectivity by FeCl3 in the Y[N(TMS)2]3-Catalyzed Transformation of Terminal Alkynes: A New Strategy for Controlling the Selectivity of Organolanthanide-Based Catalysis’, 29
K. Yoshida, I. Morimoto, K. Mitsudo, H. Tanaka (2008)
‘RhCl3/amine-catalyzed [2+2+2] cyclization of alkynes’, 64
A. C. Williams, P. Sheffels, D. Sheehan, T. Livinghouse (1989)
‘Synthetic Applications of Group V Metallacyclopropenes. Part 1. Group V Metallacyclopropenes in Synthesis. An Efficient Route to Polyfunctional Ring Systems via the Cocyclization of Diynes with Substituted Monoacetylenes’, 8
J. Li, H. Jiang, M. Chen (2001)
‘CuCl2-Induced Regiospecifical Synthesis of Benzene Derivatives in the Palladium-Catalyzed Cyclotrimerization of Alkynes’, 66
R. Maity, B. S. Birenheide, F. Breher, B. Sarkar (2021)
‘Cooperative Effects in Multimetallic Complexes Applied in Catalysis’, 13
X. Wang, Y. Liu, R. Martin (2015)
‘Ni-Catalyzed Divergent Cyclization/Carboxylation of Unactivated Primary and Secondary Alkyl Halides with CO2’, 137
J. Zhang, C. M. Medley, J. A. Krause, H. Guan (2010)
‘Mechanistic Insights into C−S Cross-Coupling Reactions Catalyzed by Nickel Bis(phosphinite) Pincer Complexes’, 29
A. Ohgi, Y. Nakao (2016)
‘Selective Hydrogenolysis of Arenols with Hydrosilanes by Nickel Catalysis’, 45
Y.-Y. Lin, S.-C. Tsai, S. J. Yu (2008)
‘Highly Efficient and Recyclable Au Nanoparticle-Supported Palladium(II) Interphase Catalysts and Microwave-Assisted Alkyne Cyclotrimerization Reactions in Ionic Liquids’, 73
N. Mori, S. Ikeda, K. Odashima (2001)
‘Chemo- and regioselective cyclotrimerization of monoynes catalyzed by a nickel(0) and zinc(II) phenoxide system’
M. Lautens, W. Klute, W. Tam (1996)
‘Transition Metal-Mediated Cycloaddition Reactions’, 96
J.-C. Hsieh, C.-H. Cheng (2008)
‘O-Dihaloarenes as aryne precursors for nickel-catalyzed [2+2+2] cycloaddition with alkynes and nitriles’
L. Xiao, Z. Chen, B. Qu, J. Luo, S. Kong, Q. Gong, J. Kido (2011)
‘Recent Progresses on Materials for Electrophosphorescent Organic Light-Emitting Devices’, 23
T. Iwayama, Y. Sato (2009)
‘Nickel(0)-catalyzed [2+2+2] cycloaddition of diynes and 3,4-pyridynes: novel synthesis of isoquinoline derivatives’
M. Aldeghi, S. Malhotra, D. L. Selwood, A. W. E. Chan (2014)
‘Two-and Three-dimensional Rings in Drugs’, 83
D. Dallinger, M. Irfan, A. Suljanovic, C. O. Kappe (2010)
‘An Investigation of Wall Effects in Microwave-Assisted Ring-Closing Metathesis and Cyclotrimerization Reactions’, 75
Y. Segawa, D. R. Levine, K. Itami (2019)
‘Topologically Unique Molecular Nanocarbons’, 52
M. Kimura, A. Miyachi, K. Kojima, S. Tanaka, Y. Tamaru (2004)
‘Highly Stereo-and Regioselective Ni-Catalyzed Homoallylation of Aldimines with Conjugated Dienes Promoted by Diethylzinc’, 126
Z. Qiu, Z. Xie (2009)
‘Nickel-Catalyzed Three-Component [2+2+2] Cycloaddition Reaction of Arynes, Alkenes, and Alkynes’, 48
V. Cadierno, S. E. García-Garrido, J. Gimeno (2006)
‘Efficient Intermolecular [2+2+2] Alkyne Cyclotrimerization in Aqueous Medium Using a Ruthenium(IV) Precatalyst’, 128
S. Saito, Y. Yamamoto (2000)
‘Recent Advances in the Transition-Metal-Catalyzed Regioselective Approaches to Polysubstituted Benzene Derivatives’, 100
S. Chakraborty, Y. J. Patel, J. A. Krause, H. Guan (2012)
‘Catalytic properties of nickel bis(phosphinite) pincer complexes in the reduction of CO2 to methanol derivatives’, 32
S. Saito, T. Kawasaki, N. Tsuboya, Y. Yamamoto (2001)
‘Highly Regioselective Cyclotrimerization of 1-Perfluoroalkylenynes Catalyzed by Nickel’, 66
Transition‐metal‐catalyzed [2+2+2] cycloaddition of alkynes is a core synthetic approach to benzene rings. Herein we describe an efficient system based on inexpensive nickel catalyst and phosphine ligand that facilitate cyclotrimerization of various internal esteryl alkynes. The regioselectivity of the protocol was precisely controlled, and a series of polysubstituted benzene rings mainly composed of 1,2,4‐isomers were provided.
Helvetica Chimica Acta – Wiley
Published: May 1, 2022
Keywords: C−C bond formation; cycloaddition; internal esteryl alkynes; nickel; catalysis; regional selectivity
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