308796-04-5Relevant academic research and scientific papers
Selective synthesis of enol ethers: Via nickel-catalyzed cross coupling of α-oxy-vinylsulfones with alkylzinc reagents
Gong, Liang,Zhang, Qian,Xie, Demeng,Zhang, Wei,Xu, Shi-Yang,Zhang, Xia,Niu, Dawen
supporting information, p. 12273 - 12276 (2021/11/30)
We describe here a Ni-catalyzed Negishi coupling reaction to prepare 1,2-dialkyl enol ethers in a stereoconvergent fashion. This method employs readily available and bench-stable α-oxy-vinylsulfones as electrophiles. The C-sulfone bond in the α-oxy-vinylsulfone motif is cleaved chemoselectively in these reactions. The mild conditions are tolerant of a variety of functional groups on both partners, thus representing a general strategy for enol ether synthesis. This unique reactivity of α-oxy-vinylsulfones indicates their further application as electrophilic partners in cross-coupling reactions.
Csp3-Csp3 Bond-Forming Reductive Elimination from Well-Defined Copper(III) Complexes
Paeth, Matthew,Tyndall, Sam B.,Chen, Liang-Yu,Hong, Jia-Cheng,Carson, William P.,Liu, Xingwu,Sun, Xiaodong,Liu, Jinjia,Yang, Kundi,Hale, Elizabeth M.,Tierney, David L.,Liu, Bin,Cao, Zhi,Cheng, Mu-Jeng,Goddard, William A.,Liu, Wei
supporting information, p. 3153 - 3159 (2019/03/06)
Carbon-carbon bond-forming reductive elimination from elusive organocopper(III) complexes has been considered the key step in many copper-catalyzed and organocuprate reactions. However, organocopper(III) complexes with well-defined structures that can undergo reductive elimination are extremely rare, especially for the formation of Csp3-Csp3 bonds. We report herein a general method for the synthesis of a series of [alkyl-CuIII-(CF3)3]- complexes, the structures of which have been unequivocally characterized by NMR spectroscopy, mass spectrometry, and X-ray crystal diffraction. At elevated temperature, these complexes undergo reductive elimination following first-order kinetics, forming alkyl-CF3 products with good yields (up to 91%). Both kinetic studies and DFT calculations indicate that the reductive elimination to form Csp3-CF3 bonds proceeds through a concerted transition state, with a ΔH? = 20 kcal/mol barrier.
A general strategy for the synthesis of enantiomerically pure azetidines and aziridines through nickel-catalyzed cross-coupling
Jensen, Kim L.,Nielsen, Dennis U.,Jamison, Timothy F.
supporting information, p. 7379 - 7383 (2015/05/13)
Abstract In this communication, we report a straightforward synthesis of enantiomerically pure 2-alkyl azetidines. The protocol is based on a highly regioselective nickel-catalyzed cross-coupling of aliphatic organozinc reagents with an aziridine that fea
