5653-09-8Relevant articles and documents
Nickel-Catalyzed Reductive Acylation of Carboxylic Acids with Alkyl Halides and N-Hydroxyphthalimide Esters Enabled by Electrochemical Process
Zhou, Xiao,Guo, Lin,Zhang, Haoxiang,Xia, Raymond Yang,Yang, Chao,Xia, Wujiong
, p. 1526 - 1531 (2022/03/31)
A sustainable Ni-catalyzed reductive acylation reaction of carboxylic acids via an electrochemical pathway is presented, affording a variety of ketones as major products. The reaction proceeds at ambient temperature using unactivated alkyl halides and N-hydroxyphthalimide (NHP) esters as coupling partners, which exhibits several synthetic advantages, including mild conditions and convenience of amplification (58% yield for 6 mmol scale reaction). (Figure presented.).
Selective catalytic synthesis of α-alkylated ketones and β-disubstituted ketones via acceptorless dehydrogenative cross-coupling of alcohols
Bhattacharyya, Dipanjan,Sarmah, Bikash Kumar,Nandi, Sekhar,Srivastava, Hemant Kumar,Das, Animesh
supporting information, p. 869 - 875 (2021/02/06)
Herein, a phosphine-free pincer ruthenium(III) catalyzed β-alkylation of secondary alcohols with primary alcohols to α-alkylated ketones and two different secondary alcohols to β-branched ketones are reported. Notably, this transformation is environmentally benign and atom efficient with H2O and H2 gas as the only byproducts. The protocol is extended to gram-scale reaction and for functionalization of complex vitamin E and cholesterol derivatives.
Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents
Geaneotes, Paul,Guo, Rui,Liu, Peng,Qi, Xiaotian,Wang, Ruihan,Wang, Yi-Ming,Xiang, Hengye
supporting information, p. 16651 - 16660 (2020/07/16)
The discovery of safe, general, and practical procedures to prepare vinyl fluorides from readily available precursors remains a synthetic challenge. The metal-free hydrofluorination of alkynes constitutes an attractive though elusive strategy for their preparation. Introduced here is an inexpensive and easily handled reagent that enables the development of simple and scalable protocols for the regioselective hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These reaction conditions were suitable for a diverse collection of alkynes, including several highly functionalized pharmaceutical derivatives. Computational and experimental mechanistic studies support C?F bond formation through vinyl cation intermediates, with the E- and Z-hydrofluorination products forming under kinetic and thermodynamic control, respectively.