30877-08-8Relevant academic research and scientific papers
MeOTf-catalyzed formal [4?+?2] annulations of styrene oxides with alkynes leading to polysubstituted naphthalenes through sequential electrophilic cyclization/ring expansion
Chen, Chao,Xi, Chanjuan,Zhang, Zeyu,Zou, Song
supporting information, (2021/12/30)
MeOTf-catalyzed formal [4 + 2] annulation of styrene oxides with alkynes to afford polysubstituted naphthalenes has been realized, which undergoes sequential electrophilic cyclization/ring expansion. A range of substrates were tolerated in the formation of naphthalene derivatives with high regioselectivity in satisfactory yields. The reaction could also be carried out on gram scale.
Metal-Free Visible-Light-Mediated Aromatization of 1,2–Dihydronaphthalenes
Rammal, Fatima,Gaumont, Annie-Claude,Lakhdar, Sami
supporting information, p. 1482 - 1485 (2019/12/12)
A series of polyaromatic naphthalenes have been synthesized through the dehydrogenation of the corresponding 1,2-dihydroarylnaphthalenes by using 9-mesityl-10-methylacridinium perchlorate as a photocatalyst and diphenyliodonium triflate as an external oxidant under visible light irradiation. The reaction proceeds smoothly under metal-free conditions and tolerates some functionalities. Interestingly, the reaction is also amenable to the aromatization of tetrahydronaphthalenes and fair conversions were obtained. Preliminary mechanistic investigations have been conducted and a reasonable mechanism is proposed.
[4 + 2] Annulation of Donor-Acceptor Cyclopropanes with Acetylenes Using 1,2-Zwitterionic Reactivity
Novikov, Roman A.,Tarasova, Anna V.,Denisov, Dmitry A.,Borisov, Denis D.,Korolev, Victor A.,Timofeev, Vladimir P.,Tomilov, Yury V.
, p. 2724 - 2738 (2017/03/14)
A new process for the [4 + 2] annulation of donor-acceptor cyclopropanes with acetylenes under the effect of anhydrous GaCl3 using 1,2-zwitterion reactivity was elaborated. The reaction opens access to substituted dihydronaphthalenes, naphthalenes, and other fused carbocycles. The direction of the reaction can be efficiently controlled by temperature.
Gold(I)-catalyzed functionalization of benzhydryl C (sp3)-H bonds
Cera, Gianpiero,Chiarucci, Michel,Dosi, Federico,Bandini, Marco
supporting information, p. 2227 - 2231 (2013/10/01)
The selective activation/functionalization of benzhydryl C (sp3) H bonds is documented. The gold complex XPhosAuNTf2 turned out to be an efficient catalyst (5 mol%) to transform readily available propargylic esters into di or trisubstituted naphthalenes i
Rhenium-catalyzed regioselective synthesis of 1,2-disubstituted naphthalenes
Umeda, Rui,Nishi, Satoru,Kojima, Aya,Kaiba, Kenta,Nishiyama, Yutaka
supporting information, p. 179 - 182 (2013/02/21)
Rhenium-catalyzed coupling reaction of alkynes with phenylacetaldehyde dimethylacetal in the presence of H2O regioselectively afforded the corresponding 1,2-disubstituted naphthalenes.
Regioselective synthesis of substituted naphthalenes and phenanthrenes by FeCl3-promoted annulation of aryl and naphthyl acetaldehydes with alkynes
Bu, Xiuli,Hong, Longcheng,Liu, Ruiting,Hong, Jianquan,Zhang, Zhengxing,Zhou, Xigeng
experimental part, p. 7960 - 7965 (2012/09/21)
The FeCl3-promoted annulation reaction of aryl acetaldehydes with alkynes has been established, which provides a new and versatile straightforward procedure for the regioselective synthesis of mono-, di-, and polysubstituted naphthalenes under mild conditions. Interestingly, the present catalytic system not only differentiates between internal and terminal alkynes but also shows unprecedented complete Me3SiOH elimination selectivity for silyl alkyne substrates. Furthermore, the synthesis of a series of substituted phenanthrenes via reactions of nathphyl acetaldehydes with internal alkynes is also achieved for the first time in good yields with excellent regioselectivity.
Palladium-catalyzed annulation of 1,2-diborylalkenes and -arenes with 1-bromo-2-[(Z)-2-bromoethenyl]arenes: A modular approach to multisubstituted naphthalenes and fused phenanthrenes
Shimizu, Masaki,Tomioka, Yosuke,Nagao, Ikuhiro,Kadowaki, Tsugumi,Hiyama, Tamejiro
experimental part, p. 1644 - 1651 (2012/09/08)
(Z)-1,2-Diaryl-1,2-bis(pinacolatoboryl)ethenes underwent double-cross-coupling reactions with 1-bromo-2-[(Z)-2-bromoethenyl]arenes in the presence of [Pd(PPh3)4] as a catalyst and 3 M aqueous Cs2CO3 as a base in THF at 80 °C. The double-coupling reaction gave multisubstituted naphthalenes in good to high yields. Annulation of 1,2-bis(pinacolatoboryl)arenes with bromo(bromoethenyl)arenes in the presence of a catalyst system that consisted of [Pd2(dba)3] (dba=dibenzylideneacetone) and 2-dicyclohexylphosphino-2′,6′- dimethoxybiphenyl (SPhos) under the same conditions produced fused phenanthrenes in good to high yields. The first annulation coupling occurred regiospecifically at the bromoethenyl moiety. This procedure is applicable to the facile synthesis of polysubstituted anthracenes, benzothiophenes, and dibenzoanthracenes through a double annulation pathway by using the corresponding dibromobis[(Z)-2-bromoethenyl]benzenes as diboryl coupling partners. Copyright
Gold(I)-catalyzed double migration cascades toward (1E,3E)-dienes and naphthalenes
Dudnik, Alexander S.,Schwier, Todd,Gevorgyan, Vladimir
scheme or table, p. 1859 - 1870 (2009/07/04)
A novel gold(I)-catalyzed cascade cycloisomerization of a variety of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This domino process involves an unprecedented tandem sequence of 1,3- and 1,2-migrations of two
Gold-Catalyzed Electrophilic Addition to Arylalkynes. A Facile Method for the Regioselective Synthesis of Substituted Naphthalenes
Balamurugan, Rengarajan,Gudla, Vanajakshi
supporting information; experimental part, p. 3116 - 3119 (2009/12/05)
An interesting gold-catalyzed electrophilic addition to arylalkyne to synthesize substituted naphthalenes has been presented. Different metal hexafluoroantimonates have also been found to effect the transformation. Counter anion and oxo- and alkynophilicities of catalytic gold species might play an important role in this annulation reaction.
Gold-catalyzed double migration-benzannulation cascade toward naphthalenes
Dudnik, Alexander S.,Schwier, Todd,Gevorgyan, Vladimir
supporting information; experimental part, p. 1465 - 1468 (2009/04/10)
(Chemical Equation Presented) A novel gold(I)-catalyzed cycloisomerization of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This cascade reaction involves an unprecedented tandem sequence of 1,3- and 1,2-migration of two different migrating groups. It is believed that this transformation likely proceeds via the formation of 1,3-diene intermediate or its precursor, which upon cyclization and aromatization steps transforms into the naphthalene core. 2008 American Chemical Society.
