92151-73-0Relevant academic research and scientific papers
Metal-Free Radical Annulation of Oxygen-Containing 1,7-Enynes: Configuration-Selective Synthesis of (E)-3-((Arylsulfonyl)methyl)-4-Substituted Arylidenechromene Derivatives
Bian, Mouwang,Dai, Lei,Mao, Kaimin,Rong, Liangce,Wang, Chang,Yu, Qiuyu,Zhang, Jinghang
supporting information, p. 218 - 224 (2021/01/13)
A novel strategy for the synthesis of (E)-3-((arylsulfonyl)methyl)-4-substituted benzylidenechromene derivatives via a metal-free radical annulation reaction of oxygen-containing 1,7-enynes with thiosulfonates has been developed. The reaction shows broad substrate scope, wide functional group tolerance, and moderate to excellent yields. Moreover, thiosulfonates were well driven to achieve the bifunctionalization reaction of oxo-1,7-enynes which derived from aliphatic alkynes. In addition, the (E)-configuration of the products was highly controlled by the structure of 1,7-enyne.
A Facile Construction of Bisheterocyclic Methane Scaffolds through Palladium-Catalyzed Domino Cyclization
Qi, Hongbo,Han, Kaiming,Chen, Shufeng
supporting information, p. 2699 - 2704 (2021/08/03)
A convenient palladium-catalyzed domino cyclization reaction for the construction of bis(benzofuranyl)methane scaffolds bearing an all-carbon quaternary center has been described. In the cascade process, one C(sp2)—O bond, two C(sp2)—C(sp3) bonds as well as two benzofuran rings are formed in a single synthetic sequence. The approach shows wide scope of substrates and good functional-group tolerance. Moreover, this methodology is successfully extended to the synthesis of benzofuranyl methyl chromane derivatives.
Photocatalyzed Coupling-Cyclization of ortho-Alkynylaryl Vinylethers with Arylsulfonyl Azides
Chen, Fengjuan,Huang, Xiang,Yang, Can,Jiang, Huanfeng,Zeng, Wei
, p. 14572 - 14585 (2021/10/25)
A novel visible-light-induced coupling-cyclization of ortho-alkynylaryl vinylethers with arylsulfonyl azides has been described. This transformation provided a concise approach to access C3-exocyclic C=C bond/C2-alkylsulfone-tethered benzofurans via a solvent-leveraged carbosulfonylation and [2 + 2 + 3] cyclization. Primary mechanistic studies demonstrated that THF belongs to a crucial H atom source.
Synthesis of diarylalkanes through an intramolecular/intermolecular addition sequence by auto-tandem catalysis with strong Br?nsted base
Kondoh, Azusa,Ma, Chaoyan,Terada, Masahiro
supporting information, p. 10894 - 10897 (2020/10/02)
An auto-tandem catalysis with a strong Br?nsted base enabled the synthesis of diarylalkanes containing a benzofuran moiety. Potassiumtert-butoxide efficiently catalyzed both the intramolecular cyclization of less acidicortho-alkynylaryl benzyl ethers and the following intermolecular addition of diarylmethanes to styrenes, demonstrating the high potential of the catalysis in organic synthesis.
Borylative Heterocyclization without Air-Free Techniques
Blum, Suzanne A.,Gao, Chao,Nakao, Shuichi
, p. 10350 - 10368 (2020/09/23)
In contrast to previously reported borylative heterocyclization methods, a reaction here proceeds without air-free techniques to access synthetically useful borylated thiophenes, benzothiophenes, and isocoumarins. A comparison of stability/decomposition rates in air of several catecholboronic ester (Bcat) compounds derived from different heterocycle cores showed a strong dependence on the heterocycle structure. Lessons learned from this comparison were then harnessed for the development of borylative heterocyclization reactions under ambient-atmosphere conditions and with wet solvent. In contrast to literature reports suggesting general moisture sensitivity, a subset of Bcat products resulting from this technique were chromatography-stable and directly isolable, obviating the requirement for an extra synthetic transformation into more stable boron species, such as pinacolboronic esters (Bpin), for isolation. The isolated Bcat products were amenable to various downstream functionalization reactions, including reactions that were not accessible with their better-known Bpin counterparts, showing the complementarity of Bcat reaction partners and expanding their known chemistry. These results suggest the value of conceptual revisitation of substitution and solvent influence on stability and isolability of organo-Bcat compound classes and lay the groundwork for development of additional practical borylative methods in air.
One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols
Akai, Shuji,Ikawa, Takashi,Masuda, Shigeaki
, (2020/03/23)
Benzynes were selectively generated in situ from phenols and trapped regioselectively with potassium hexamethyldisilazide to form primary anilines following acidic workup. The direct conversion of a phenolic hydroxyl group into a free amino group is a useful method for the preparation of primary aryl amines that are hard to synthesize by using coupling reactions involving phenol derivatives with ammonia. Whereas reactions of ortho- and meta-substituted phenols produced meta-substituted anilines exclusively, those of para-substituted phenols provided ortho-silylanilines.
Thermal [2 + 2]-cycloaddition between silylalkynes and allenylphenols followed by the nucleophilic addition of water: Metal-free and economical synthesis of arylcyclobutenals
Ohno, Shohei,Avena, Ramon Francisco,Aoyama, Hiroshi,Fujioka, Hiromichi,Arisawa, Mitsuhiro
, p. 1220 - 1228 (2020/03/11)
Herein, we report an unprecedented thermal [2 + 2]-cycloaddition between silylalkynes and allenylphenols to form an aromatizing cyclobutachromene intermediate, followed by the nucleophilic addition of water to yield functionalized arylcyclobutenals. This reaction is atom- and pot-economical because all the atoms contained in the starting material are retained in the final product, no other reactants are required, and it proceeds in one-pot.
Palladium complexes with an annellated mesoionic carbene (MIC) ligand: Catalytic sequential Sonogashira coupling/cyclization reaction for one-pot synthesis of benzofuran, indole, isocoumarin and isoquinolone derivatives
Bera, Jitendra K.,Daw, Prosenjit,Reshi, Noor U Din,Tyagi, Akshi
supporting information, p. 15238 - 15248 (2020/11/18)
Two Pd(ii) complexes (1 and 2) featuring a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand have been synthesized and structurally characterized. Both complexes effectively catalyze the one-pot synthesis of benzofuran starting from phenylacetylene and 2-iodophenol under mild conditions. Complex 1 is found to be an excellent catalyst for the straightforward access to a library of benzofuran, indole, isocoumarin and isoquinolone derivatives by the reaction of terminal alkynes with 2-iodo derivates of phenol, N-methyl aniline, benzoic acid and N-methyl benzamide, respectively. The general utility of the catalytic method is demonstrated using a variety of diversely substituted terminal alkynes and the corresponding desired products are obtained in good to excellent yields. On the basis of control experiments, a two-cycle mechanism is proposed which involves the Sonogashira coupling of 2-iodo derivatives with alkynes and the subsequent cyclization of the corresponding 2-alkynyl compounds.
Application of compound containing trifluoromethyl indeno benzo six-membered heterocyclic structure in prevention and treatment of plant diseases and pests
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Paragraph 0044-0046, (2020/07/02)
The invention relates to application of a compound containing a trifluoromethyl indeno benzo six-membered heterocyclic structure in prevention and treatment of plant diseases and pests. The significance of each group in the formula is shown in the specifi
Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes
Liang, Hao,He, Xiaobo,Zhang, Yaqi,Chen, Bin,Ouyang, Jia-Sheng,Li, Yongsu,Pan, Bendu,Subba Reddy, Chitreddy V.,Chan, Wesley Ting Kwok,Qiu, Liqin
supporting information, p. 11429 - 11432 (2020/10/12)
The copper(ii)-catalyzed (4+1) cyclizations and copper(i)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionaliz
