70650-50-9Relevant academic research and scientific papers
Alkene Difunctionalization Triggered by a Stabilized Allenyl Radical: Concomitant Installation of Two Unsaturated C?C Bonds
Wei, Yunlong,Wu, Xinxin,Zhang, Hong,Zhu, Chen
, p. 20215 - 20219 (2021)
Radical-mediated difunctionalization of alkenes provides a promising approach to introduce one alkenyl or alkynyl group to target compounds. However, simultaneous installation of two unsaturated C?C bonds via alkene difunctionalization remains elusive, at
Selectivity for Alkynyl or Allenyl Imidamides and Imidates in Copper-Catalyzed Reactions of Terminal 1,3-Diynes and Azides
Ghorai, Sourav,Lee, Daesung
supporting information, p. 697 - 701 (2021/02/01)
Copper-catalyzed reactions of terminal 1,3-diynes with electron-deficient azides to generate either 3-alkynyl or 2,3-dienyl imidamides and imidates are described. The selectivity depends on the diyne substituents and the nucleophile that reacts with the ketenimide intermediate generated from the corresponding triazole precursor. Reactions of 1,3-diynes containing a propargylic acetate afford [3]cumulenyl imidamides, while reactions using methanol as the trapping agent selectively generate 2,3-dienyl imidates. Five-membered heterocycles were obtained from 1,3-diynes containing a homopropargylic hydroxyl or amine substituent.
Synthesis of α-Acyloxy-α′-hydroxy Ketones via Cyclic Carbonate Intermediates Generated from Tertiary Bromopropargylic Alcohols and Cs2CO3
Shemyakina, Olesya A.,Volostnykh, Ol'ga G.,Stepanov, Anton V.,Ushakov, Igor' A.
supporting information, p. 7117 - 7121 (2019/11/16)
A facile approach towards α-acyloxy-α′-hydroxy ketones by reaction of readily available tertiary bromopropargylic alcohols and carboxylic acids in system Cs2CO3/H2O/DMF (50–55 °C, 4 h) was developed. Key intermediates of this synthesis are cyclic carbonates generated in situ from bromopropargylic alcohols and Cs2CO3 which have been utilized as both reagent and base promoter.
Palladium-catalyzed bond reorganization of 1,3-diynes: An entry to diverse functionalized 1,5-dien-3-ynes
Wu, Wanqing,Gao, Yang,Jiang, Huanfeng,Huang, Yubing
supporting information, p. 4580 - 4586 (2013/06/05)
A mild and efficient method for the synthesis of functionalized 1,5-dien-3-ynes from 1,3-diynes under PdII catalysis is described. The process allows quick and atom-economical assembly of various dihalo-, haloacyl-, and diacyl-substituted 1,5-dien-3-ynes in high yields. The switch of selectivity in the formation of these dienyne products can be controlled by the choice of catalysis system and reaction conditions.
Palladium-catalyzed bromoalkynylation of C-C double bonds: Ring-structure-dependent synthesis of 7-alkynyl norbornanes and cyclobutenyl halides
Li, Yibiao,Liu, Xiaohang,Jiang, Huanfeng,Liu, Bifu,Chen, Zhengwang,Zhou, Peng
supporting information; experimental part, p. 6341 - 6345 (2011/09/13)
Strain versus flexibility: The palladium-catalyzed reaction of haloalkynes with norbornene derivatives leads to 7-alkynyl norbornane products (see scheme). Key to the success of this reaction is the formation of a "bridging" palladium species, which can rearrange to result in a C-7 functionalization. The ring-structure-dependent [2+2] cycloaddition of haloalkynes with cyclooctene has been achieved in moderate to good yields under similar conditions. Copyright
