1415461-91-4Relevant academic research and scientific papers
A one-pot method for the synthesis of phenylalkynyl-substituted terminal alkynes by deprotection/stannylation followed by a Migita-Kosugi-Stille coupling
Peng, Li-Fen,Wang, Bing-Hao,Wang, Ming,Tang, Zi-Long,Jiang, Yan-Zi,Jiao, Yin-Chun,Xu, Xin-Hua
, p. 235 - 238 (2018)
A practical one-pot approach for the synthesis of arylalkynyl-substituted terminal alkynes has been developed through a deprotection/ stannylation of a phenylethynyl phosphine oxide followed by Migita-Kosugi-Stille coupling, avoiding the longer synthetic route involving repeated deprotection/Sonogashira coupling. Other features of this approach include mild reaction conditions, excellent yields, facile isolation of products and wide functional group tolerance.
Synthesis of Naphthalenyl Triflates via the Cationic Annulation of Benzodiynes with Triflic Acid
Ge, Chenxin,Wang, Guohua,Wu, Panpan,Chen, Chao
supporting information, p. 5010 - 5014 (2019/07/08)
A highly efficient and regioselective annulation of benzodiynes promoted by triflic acid has been developed. This protocol provides a step and atom-economic access to a series of naphthalenyl triflates. Furthermore, direct synthetic applications of this r
The Gold(I)-Mediated Domino Reaction to Fused Diphenyl Phosphoniumfluorenes: Mechanistic Consequences for Gold-Catalyzed Hydroarylations and Application in Solar Cells
Arndt, Sebastian,Borstelmann, Jan,Eshagh Saatlo, Rebeka,Antoni, Patrick W.,Rominger, Frank,Rudolph, Matthias,An, Qingzhi,Vaynzof, Yana,Hashmi, A. Stephen K.
supporting information, p. 7882 - 7889 (2018/06/15)
A domino sequence, involving a phosphinoauration and a gold-catalyzed 6-endo-dig cyclization step, was developed. Starting from modular and simple-to-prepare phosphadiynes, π-extended phosphoniumfluorenes were synthesized. The mechanistic proposal was sup
Complex Annulations through Silver Carbenoid Intermediate: An Alternative Entry to Transformations of 1,2,3-Triazoles
Yang, Yuan,Yu, Jiang-Xi,Ouyang, Xuan-Hui,Li, Jin-Heng
supporting information, p. 3982 - 3985 (2017/08/14)
An alternative entry to transformations of N-sulfonyl-4-(2-(ethynyl)aryl)-1,2,3-triazoles with various generated in situ or external nucleophiles by means of silver catalysis for producing diverse functionalized isoquinolines is described. Mechanistically
Insights into the Gold-Catalyzed Propargyl Ester Rearrangement/Tandem Cyclization Sequence: Radical versus Gold Catalysis - Myers-Saito- versus Schmittel-Type Cyclization
Rettenmeier, Eva,Hansmann, Max M.,Ahrens, Alexander,Rübenacker, Katharina,Saboo, Tapish,Massholder, Joy,Meier, Christian,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 14401 - 14409 (2015/10/05)
A detailed study of the gold-catalyzed tandem 1,3-carboxy migration/allene-enyne cycloisomerization was undertaken. It was found that after the initial allene formation the selectivity of the reaction is strongly influenced by the polarization of the remaining alkyne. Depending on the substitution pattern of the starting diynes, either a Schmittel- or a Myers-Saito-type cyclization was triggered. The 6-endo-dig Myers-Saito-type cyclization gave access to benzo[b]fluorenes, while the Schmittel pathway (5-exo-dig) delivered benzofulvenes as final products. In special cases a yet unknown pathway was opened by the ambiphilic nature of the allene moiety. In these cases completely different products were obtained by the nucleophilic attack of the alkyne moiety onto the allene that can also act as an electrophile. Mechanistic studies revealed that diradical pathways can be ruled out for this type of tandem cyclization reactions and it is shown that both steps of the reaction cascade are catalyzed by the gold complex.
Grignard reagent/CuI/LiCl-mediated stereoselective cascade addition/cyclization of diynes: A novel pathway for the construction of 1-methyleneindene derivatives
Li, De-Yao,Wei, Yin,Shi, Min
, p. 15682 - 15688 (2013/11/19)
Diynes containing a cyclopropane group smoothly undergo a novel intramolecular and stereoselective cascade addition/cyclization reaction to produce the corresponding 1-methyleneindene derivatives in moderate to good yields. This interesting transformation is mediated by Grignard reagent/CuI with LiCl as an additive under mild conditions. The obtained product can easily be further functionalized through cyclopropyl ring opening. A plausible reaction mechanism has also been presented on the basis of deuterium labeling and control experiments. Diyne cyclization: Diynes containing a cyclopropane group undergo a novel intramolecular and stereoselective cascade addition/cyclization reaction to produce the corresponding 1-methyleneindene derivatives (see scheme). The transformation proceeds under mild conditions and is promoted by a combination of Grignard reagent Copyright
Polyaromatic ribbon/benzofuran fusion via consecutive endo cyclizations of enediynes
Byers, Philip M.,Rashid, Julian I.,Mohamed, Rana K.,Alabugin, Igor V.
supporting information, p. 6032 - 6035 (2013/02/22)
The Sonogashira/5-endo-dig/6-endo-dig cascade fuses a polycyclic aromatic backbone to the electron-rich furan subunit. The transformation proceeds in modest yields as a one-pot reaction. Efficiency of the full cascade is increased by removal of base prior
