1268468-01-4Relevant academic research and scientific papers
Chemodivergent Synthesis of One-Carbon-Extended Alcohols via Copper-Catalyzed Hydroxymethylation of Alkynes with Formic Acid
Jin, Xin,Fu, Hong-Chen,Wang, Mei-Yan,Huang, Shouying,Wang, Yue,He, Liang-Nian,Ma, Xinbin
supporting information, p. 4997 - 5001 (2021/06/28)
The development of selective catalytic reactions that utilize easily available reagents for the efficient synthesis of alcohols is a long-standing goal of chemical research. Here an intriguing strategy for the chemodivergent copper-catalyzed hydroxymethylation of alkynes with formic acid and hydrosilane has been developed. By simply tuning the amount of formic acid and reaction temperature, distinct one-carbon-extended primary alcohols, that is, allylic alcohols and β-branched alkyl alcohols, were produced with high levels of Z/E-, regio-, and enantioselectivity.
Copper-Catalyzed and Proton-Directed Selective Hydroxymethylation of Alkynes with CO2
Wang, Mei-Yan,Jin, Xin,Wang, Xiaofei,Xia, Shumei,Wang, Yue,Huang, Shouying,Li, Ying,He, Liang-Nian,Ma, Xinbin
supporting information, p. 3984 - 3988 (2020/12/25)
An intriguing strategy for copper-catalyzed hydroxymethylation of alkynes with CO2 and hydrosilane was developed. Switched on/off a proton source, for example, tBuOH, direct hydroxymethylation and reductive hydroxymethylation could be triggered selectively, delivering a series of allylic alcohols and homobenzylic alcohols, respectively, with high levels of Z/E, regio- and enantioselectivity. Such a selective synthesis is attributed to the differences in response of vinylcopper intermediate to proton and CO2. The protonation of vinylcopper species is demonstrated to be prior to hydroxymethylation, thus allowing a diversion from direct alkyne hydroxymethylation to reductive hydroxymethylation in the presence of suitable proton.
Copper-catalyzed hydrocarboxylation of alkynes using carbon dioxide and hydrosilanes
Fujihara, Tetsuaki,Xu, Tinghua,Semba, Kazuhiko,Terao, Jun,Tsuji, Yasushi
, p. 523 - 527 (2011/03/16)
Getting a fix: The copper-catalyzed hydrocarboxylation of alkynes using carbon dioxide in the presence of a hydrosilane, which serves as a reducing agent, has been developed (see scheme). Copper fluorides bearing N-heterocyclic carbene ligands such as IMes and Cl2IPr show high catalytic activities.
