91295-77-1Relevant academic research and scientific papers
Nickel-catalyzed reductive defluorination of iodo allylic: Gem -difluorides: Allenyl monofluoride synthesis
You, Yiming,Wu, Jiayue,Yang, Lixin,Wu, Tao
supporting information, p. 1970 - 1973 (2022/02/19)
As a potential fluorinated synthon, there have been only limited reports on fluorinated allene synthesis and applications due to concerns about their stability. Here, we developed a nickel-catalyzed reductive defluorination of iodo allyl gem-difluorides to afford allenyl monofluorides under mild conditions with good functional group tolerance, which were easily converted to other C-F bond compounds, such as alkyl and alkenyl fluorides. Preliminary mechanistic studies suggested that monofluoroallenes were yielded by β-F elimination of the alkenyl C-Ni intermediates from the oxidative addition of C-I bonds to a nickel(0) catalyst, while zinc regenerates the catalyst and closes the catalytic cycle.
Catalytic Access to Functionalized Allylic gem-Difluorides via Fluorinative Meyer–Schuster-Like Rearrangement
An, Rui,Li, Huimin,Liao, Lihao,Wu, Jin-Ji,Xu, Yang,Zhao, Xiaodan
supporting information, p. 11010 - 11019 (2020/05/18)
An unprecedented approach for efficient synthesis of functionalized allylic gem-difluorides via catalytic fluorinative Meyer–Schuster-like rearrangement is disclosed. This transformation proceeded with readily accessible propargylic fluorides, and low-cost B–F reagents and electrophilic reagents by sulfide catalysis. A series of iodinated, brominated, and trifluoromethylthiolated allylic gem-difluorides that were difficult to access by other methods were facilely produced with a wide range of functional groups. Importantly, the obtained iodinated products could be incorporated into different drugs and natural products, and could be expediently converted into many other valuable gem-difluoroalkyl molecules as well. Mechanistic studies revealed that this reaction went through a regioselective fluorination of alkynes followed by a formal 1,3-fluorine migration under the assistance of the B–F reagents to give the desired products.
A palladium nanoparticle-nanomicelle combination for the stereo-selective semihydrogenation of alkynes in water at room temperature
Slack, Eric D.,Gabriel, Christopher M.,Lipshutz, Bruce H.
supporting information, p. 14051 - 14054 (2015/02/19)
The addition of NaBH4 to Pd(OAc) 2 in water containing nanomicelles leads to the generation of H2 and Pd nanoparticles. Subsequent reduction of disubstituted alkynes affords Z-alkenes in high yields. These reactions are general, take place in water at ambient temperatures, and offer recycling of the aqueous reaction mixture along with low overall E Factors.
Iridium-catalyzed [2+2+2] cycloaddition of α,ω-diynes with alkynyl ketones and alkynyl esters
Hashimoto, Toru,Okabe, Arisa,Mizuno, Takeshi,Izawa, Mao,Takeuchi, Ryo
supporting information, p. 8681 - 8689 (2015/01/09)
We found that the combination of [Ir(cod)Cl]2 and rac-BINAP served as an efficient catalyst for the [2+2+2] cycloaddition of 2,7-nonadiyne derivatives and related compounds with alkynyl ketones and alkynyl esters. The corresponding products wer
Studies on Pd(II)-catalyzed synthesis of (Z)-α-haloalkylidene-β- lactones from cyclocarbonylation of 2-alkynols and the subsequent coupling reactions
Ma, Shengming,Wu, Bin,Jiang, Xuefeng,Zhao, Shimin
, p. 2568 - 2575 (2007/10/03)
(Chemical Equation Presented) A good regio- and stereoselectivity was observed for the PdCl2-catalyzed cyclocarbonylation of 2-alkynols with CuCl2 affording (Z)-α-chloroalkylidene-β-lactones. The highly optically active (Z)-α-chloroa
