2050-23-9Relevant articles and documents
Reductive Alkylation of Alkenyl Acetates with Alkyl Bromides by Nickel Catalysis
Bai, Yunfei,Han, Guan-Yu,He, Rong-De,Liu, Xue-Yuan,Pan, Xiaobo,Pang, Xiaobo,Shu, Xing-Zhong,Zhao, Zhen-Zhen
supporting information, (2021/12/14)
Catalytic alkylation of stable alkenyl C?O electrophiles is synthetically appealing, but studies to date have typically focused on the reactions with alkyl Grignard reagents. We report herein a cross-electrophile reaction of alkenyl acetates with alkyl bromides. This work has enabled a new method for the synthesis of aliphatic alkenes from alkenyl acetates to be established that can be used to add more structural complexity and molecular diversity with enhanced functionality tolerance. The method allows for a gram-scale reaction and modification of biologically active molecules, and it affords access to useful building blocks. Preliminary mechanistic studies reveal that the NiI species plays an essential role for the success of the coupling of these two reactivity-mismatched electrophiles.
Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates
Mills, L. Reginald,Zhou, Cuihan,Fung, Emily,Rousseaux, Sophie A. L.
supporting information, p. 8805 - 8809 (2019/11/03)
Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.
Cobalt-Catalyzed Csp3?Csp3Homocoupling
Cai, Yingxiao,Qian, Xin,Gosmini, Corinne
supporting information, p. 2427 - 2430 (2016/08/16)
An efficient and easy method for Csp3?Csp3homocoupling was developed using cobalt bromide as catalyst. A series of functionalized alkyl bromides and alkyl chlorides were coupled in high yields under mild conditions. This reaction seems to involve a radical intermediate. (Figure presented.).
