A novel electromagnetic mill promoted mechanochemical solid-state Suzuki–Miyaura cross-coupling reaction using ultra-low catalyst loading
作者:Xin Li、Yunxia Liu、Lizhi Zhang、Yunhui Dong、Qing Liu、Daopeng Zhang、Lei Chen、Zengdian Zhao、Hui Liu
DOI:10.1039/d2gc01427k
日期:——
The Nobel-prize-winning Suzuki–Miyauracross-coupling (SMC) is a practical and attractive strategy for the construction of C–C bonds in both academic and industrial settings. However, the development of solid-state SMC reactions remains extremely scarce. Herein, we report an electromagnetic mill (EMM) promoted solid-state SMC reactionusing ultra-low palladium loading (0.05 mol%) without any liquid
The actually direct Suzuki-Miyaura coupling with "protected" R-B(dan) (dan = naphthalene-1,8-diaminato) was demonstrated to smoothly occur without in situ deprotection of the B(dan) moiety. The use of t-BuOK (Ba(OH)(2) in some cases) as a base under anhydrous conditions is the key to the successful cross-coupling, where R B(dan) is readily converted into a transmetalation-active borate-form, regardless of the well-accepted diminished boron-Lewis acidity.
Shirakawa, Hideki; Kadokura, Yasuo; Goto, Hiromasa, Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 255, p. 213 - 220