1310329-75-9Relevant academic research and scientific papers
Visible-Light-Promoted Formation of C—C and C—P Bonds Derived from Evolution of Bromoalkynes under Additive-Free Conditions: Synthesis of 1,1-Dibromo-1-en-3-ynes and Alkynylphosphine Oxides
Xu, Hailong,Chen, Rui,Ruan, Hongjie,Ye, Ruyi,Meng, Ling-Guo
, p. 873 - 878 (2021/03/04)
The controllable achievement of C—C and C—P bond formations is developed via visible-light-promoted bromoalkyne dimerization or its further transformation with secondary phosphine oxides. The 1,1-dibromo-1-en-3-ynes are formed when bromoalkyne is exposed to visible-light. While alkynylphosphine oxides are generated when bromoalkynes are mixed with secondary phosphine oxides.
Electrochemical Sulfonylation of Alkynes with Sulfonyl Hydrazides: A Metal- and Oxidant-Free Protocol for the Synthesis of Alkynyl Sulfones
Mo, Zu-Yu,Zhang, Yu-Zhen,Huang, Guo-Bao,Wang, Xin-Yu,Pan, Ying-Ming,Tang, Hai-Tao
, p. 2160 - 2167 (2020/03/04)
Herein, an electrochemical oxidative cross-coupling reaction between terminal alkynes and sulfonylhydrazides has been developed. Tetrabutylammonium iodide is used as the electrolyte and redox medium. The significant advantages of this method are high atom efficiency, functional group tolerance, and transition metal- and oxidant-free conditions. Most of the compounds exhibit good inhibitory activity on tumor cell lines, and one of the compounds can inhibit cell migration and induce apoptosis in HeLa cells. (Figure presented.).
Azobisisobutyronitrile-Initiated Oxidative C-H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[ b]phosphole Oxides and 6 H-Indeno[2,1- b]phosphindole 5-Oxide Derivatives
Guo, Jiami,Mao, Chenlu,Deng, Bin,Ye, Liyi,Yin, Yingwu,Gao, Yuxing,Tu, Song
, p. 6359 - 6371 (2020/07/14)
The first metal-free and facile radical addition/cyclization of simple alcohols with diaryl(arylethynyl)phosphine oxides has been described with azobisisobutyronitrile as a radical initiator, affording an efficient and one-pot procedure to access a new cl
Additive-free coupling of bromoalkynes with secondary phosphine oxides to generate alkynylphosphine oxides in acetic anhydride
Ruan, Hongjie,Meng, Ling-Guo,Xu, Hailong,Liang, Yuqing,Wang, Lei
supporting information, p. 1087 - 1090 (2020/02/22)
A coupling of bromoalkynes with secondary phosphine oxides was developed for the synthesis of alkynylphosphine oxides. This transformation was accomplished under additive-free conditions in acetic anhydride (Ac2O). The reaction could be carried out under mild conditions, and a wide range of secondary phosphine oxides were obtained in good yields.
Silver-Free Direct Synthesis of Alkynylphosphine Oxides via spC-H/P(O)-H Dehydrogenative Coupling Catalyzed by Palladium
Zhang, Jian-Qiu,Chen, Tieqiao,Zhang, Ji-Shu,Han, Li-Biao
supporting information, p. 4692 - 4695 (2017/09/11)
A silver-free palladium-catalyzed dehydrogenative phosphorylation of terminal alkynes with hydrogen phosphine oxides has been developed. Both aromatic and aliphatic terminal alkynes including those bearing functional groups coupled readily with hydrogen phosphine oxides, producing the corresponding value-added alkynylphosphine oxides in good to excellent yields. This reaction could be easily conducted at gram scales (10 mmol) without any decrease of the reaction efficiency, showing highly potential synthetic value in organic synthesis. A plausible Pd(0)/Pd(II) mechanism is proposed.
Regioselective Synthesis of Heteroatom-Functionalized Cyclobutene-triflones and Cyclobutenones
Alcaide, Benito,Almendros, Pedro,Lázaro-Milla, Carlos
, p. 2630 - 2639 (2017/08/16)
The controlled metal-free synthesis of a vast variety of heteroatom-containing cyclobutene-triflones [bis(trifluoromethylsulfonyl)cyclobutenes] and cyclobutenones has been developed starting from heteroatom-substituted alkynes and a pyridinium salt (a latent Tf2C=CH2 source). This powerful methodology, involving cyclization reactions, allows for the selective preparation of oxygen-, nitrogen-, bromine-, chlorine-, iodine-, sulfur-, selenium-, tellurium-, phosphorus-, and silicon-functionalized cyclobutene derivatives. (Figure presented.).
Catalyst- and Oxidant-Free Desulfonative C?P Couplings for the Synthesis of Phosphine Oxides and Phosphonates
Guo, Hong-Mei,Zhou, Quan-Quan,Jiang, Xuan,Shi, De-Qing,Xiao, Wen-Jing
supporting information, p. 4141 - 4146 (2017/10/09)
An efficient and practical approach towards phosphine oxides and phosphonates has been successfully developed through the desulfonative coupling of various sulfones with secondary phosphine oxides and phosphites. This protocol features simple experimental
Room-Temperature Alkynylation of Phosphine Oxides with Copper Acetylides: Practical Synthesis of Alkynylphosphine Oxides
Gérard, Phidéline,Veillard, Romain,Alayrac, Carole,Gaumont, Annie-Claude,Evano, Gwilherm
, p. 633 - 638 (2017/01/18)
An efficient procedure for the synthesis of alkynylphosphine oxides based on the oxidative alkynylation of secondary phosphine oxides with copper acetylides was developed. Activation with molecular oxygen in the presence of either a mixture of 1,2-dimethylimidazole and triethylamine or N-methylimidazole alone enabled the formal umpolung of the poorly nucleophilic copper acetylides, which were coupled with phosphine oxides under remarkably mild conditions. Notable features of this procedure are the availability of the starting materials, its user-friendliness, and its mild conditions, which allow the synthesis of complex alkynylphosphine oxides.
Silver-Mediated Selective Oxidative Cross-Coupling between C-H/P-H: A Strategy to Construct Alkynyl(diaryl)phosphine Oxide
Wang, Tao,Chen, Songtao,Shao, Ailong,Gao, Meng,Huang, Yangfei,Lei, Aiwen
supporting information, p. 118 - 121 (2015/07/28)
(Formula Presented) A direct oxidative cross-coupling between terminal alkynes and secondary phosphine oxides was developed. This approach provides an efficient way to construct alkynyl di(phenyl) phosphine oxides from basic materials, and in this process
Selective deprotection of Me3Si-/Ph2P(O)-protected arylalkynes: Methyl Grignard reagent-promoted dephosphorylation of Ph2P(O)-protected alkynes
Peng, Lifen,Xu, Feng,Shinohara, Kenta,Orita, Akihiro,Otera, Junzo
, p. 1610 - 1612 (2014/12/11)
A Ph2P(O)-protected alkyne underwent dephosphorylation by treatment with MeMgBr in THF with Me3Si-protection untouched. The dephosphorylation followed by a transition-metal-catalyzed coupling of the resulting terminal a lkyne with aryl halides was carried out in a one-pot manner to afford the desired coupling product. Selective deprotection of Me3Si-/Ph2P(O)-protected alkynes enabled facile syntheses of expanded π-systems such as cyclic phenyleneethyny lenes and unsymmetrically substituted ditriazol.
