33675-43-3Relevant 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
supporting information, 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.
Fully Substituted Conjugate Benzofuran Core: Multiyne Cascade Coupling and Oxidation of Cyclopropenone
Yao, Liangliang,Hu, Qiong,Bao, Li,Zhu, Wenjing,Hu, Yimin
supporting information, p. 4971 - 4975 (2021/06/30)
An unprecedented C═C double bond cleavage of cyclopropenone and dioxygen activation by multiyne cascade coupling has been developed. This chemistry provides a novel, simple, and efficient approach to synthesize fully substituted conjugate benzofuran derivatives from simple substrates under mild conditions. The density functional theory (DFT) calculations reveal that the unique homolytic cleavages of cyclopropenone and molecular oxygen are crucial to the success of this reaction.
Palladium-Catalyzed Carbonylation in the Synthesis of N-Ynonylsulfoximines
Ma, Ding,Wang, Chenyang,Kong, Deshen,Tu, Yongliang,Shi, Peng,Bolm, Carsten
supporting information, p. 1330 - 1334 (2021/01/26)
Palladium-catalyzed carbonylation reactions with Cr(CO)6 as carbonyl source are key for the preparation of N-ynonylsulfoximines from NH-sulfoximines and bromoalkynes. The couplings proceed at room temperature with a wide range of substrate combinations affording the corresponding products in good yields. (Figure presented.).
Access to Benzoxazepines and Fully Substituted Indoles via HDDA Coupling
Zheng, Xiaojie,Liu, Baohua,Yang, Feihu,Hu, Qiong,Yao, Liangliang,Hu, Yimin
supporting information, p. 956 - 959 (2020/02/15)
The HDDA-derived benzyne intermediate was captured by oxazolines based on the addition reaction of benzyne to the Ca?N double bond. Benzoxazepine derivatives, fused benzoxazepine derivatives, and fully substituted indoles are synthesized in one step. The reaction does not require any catalyst or additives. Possible reaction mechanisms are presented.
Phenanthrenes/dihydrophenanthrenes: The selectivity controlled by different benzynes and allenes
Yao, Liangliang,Fang, Bo,Hu, Qiong,Lei, Yu,Bao, Li,Hu, Yimin
supporting information, p. 15185 - 15188 (2020/12/21)
A method for the intermolecular annulation of benzynes with allenes is disclosed. This protocol utilized allenes as an unconventional diene component for the selective synthesis of phenanthrenes and dihydrophenanthrenes under the control of different benzyne precursors, featuring high atom-economy and good functional group compatibility. Density functional theory (DFT) calculations reveal that different migratory routes of the aromatic C-H bond are crucial for the observed selectivity. This journal is
Visible-Light-Promoted Oxo-Sulfonylation of Ynamides with Sulfonic Acids
Wang, Lu,Lu, Chengrong,Yue, Yanni,Feng, Chao
supporting information, p. 3514 - 3517 (2019/05/16)
A visible-light-promoted oxo-sulfonylation of ynamides with sulfonic acids is reported, giving rise to a collection of functionalized α-sulfonylated amides in a straightforward manner. The reaction proceeds sequentially through a cascade of electrophilic addition and photoinduced sulfonyl radical-sustained skeleton rearrangement. The high atom economy, mild reaction conditions, and wide substrate scope comprised the merits of this synthetic transformation.
Nickel-Catalyzed Reductive 1,2-Dialkynylation of Alkenes Bearing an 8-Aminoquinoline Directing Group
Pan, Rui,Shi, Cong,Zhang, Dongquan,Tian, Yang,Guo, Songjin,Yao, Hequan,Lin, Aijun
supporting information, p. 8915 - 8920 (2019/11/14)
An unprecedented nickel-catalyzed reductive 1,2-dialkynylation of alkenes bearing an 8-aminoquinoline directing group has been developed. This method proceeded through a migratory insertion/reductive-coupling process under mild conditions with a wide substrate scope and good functional group tolerance, providing direct access to the synthetically flexible 1,5-diynes. Moreover, the 1,2-dialkynylation products could be further converted to borate-ester- or azide-functionalized 1,5-dienes, ditriazole, β-diyne primary amide, and trisubstituted benzene.
A Micellar Catalysis Strategy for Amidation of Alkynyl Bromides: Synthesis of Ynamides in Water
Yang, Yunqin,Meng, Xiangtai,Zhu, Baolong,Jia, Ying,Cao, Xiaoji,Huang, Shenlin
supporting information, p. 1166 - 1169 (2019/01/04)
Copper-catalyzed amidation of alkynyl bromides can be carried out in water for the first time, which is made possible by a micellar catalysis strategy using rosin-based surfactant APGS-550-M. The surfactant can be easily prepared from natural abundant biomass, resin acids. Studies as to substrate scope and reaction aqueous medium recycling showcase the ease and sustainability of this technology.
Gold(III)-catalyzed chemoselective annulations of anthranils with N-allylynamides for the synthesis of 3-azabicyclo[3.1.0]hexan-2-imines
Song, Lina,Tian, Xianhai,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 9007 - 9010 (2019/08/01)
We herein report the gold(iii)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions. By trapping the in situ-generated α-imino gold carbenes, 3-azabicyclo[3.1.0]hexan-2-imines were obtained in high synthetic efficiency. The reaction, which can be conducted in the gram scale, tolerates electron-rich and electron-deficient anthranils as well as a diverse set of functionalized ynamides (aryl- and alkyl-substituted terminal).
Visible Light-Induced Difunctionalization of Alkynes: The Synthesis of Thiazoles and 1,1-Dibromo-1-en-3-ynes
Huang, Xiaoying,Chen, Hui,Huang, Zhongzhi,Xu, Yanli,Li, Fangyao,Ma, Xianli,Chen, Yanyan
, p. 15283 - 15293 (2019/12/04)
A visible light-induced cascade cyclization of thioamides with alkynes was developed to synthesize 1,3-thiozoles. The sulfur radical generated from thioamide via the single-electron transfer (SET) pathway was promoted by photocatalysis as a key intermediate in this reaction. When bromoalkynes were used as the substrate, the self-coupling products 1,1-dibromo-1-en-3-ynes were obtained in moderate yields, and an energy transfer pathway for this transformation promoted by visible-light photocatalysis was proposed.
