- Ortho-substitution groups promoted photo-induced E (trans) → Z (cis) isomerization
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The past decades have witnessed the fast growth of ortho-directing group assisted in C[sbnd]H activation and olefination. Herein we addressed these olefination products’ photo-induced E → Z isomerization in term of various ortho-substitution groups. Initi
- Cui, He-Zhen,Hong, Xi,Hou, Xiu-Feng,Reheman, Aikebaier,Sun, Yong,Zhan, Bing,Zhou, Quan
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- Nickel-catalyzed Suzuki-Miyaura reaction of aryl fluorides
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Two protocols for the nickel-catalyzed cross-coupling of aryl fluorides with aryl boronic esters have been developed. The first employs metal fluoride cocatalysts, such as ZrF4 and TiF4, which enable Suzuki-Miyaura reactions of aryl fluorides bearing electron-withdrawing (ketones, esters, and CF3), aryl and alkenyl groups as well as those comprising fused aromatic rings, such as fluoronaphthalenes and fluoroquinolines. The second protocol employs aryl fluorides bearing ortho-directing groups, which facilitate the difficult C-F bond activation process via cyclometalation. N-heterocycles, such as pyridines, quinolines, pyrazoles, and oxazolines, can successfully promote cross-coupling with an array of organoboronic esters. A study into the substituent effects with respect to both coupling components has provided fundamental insights into the mechanism of the nickel-catalyzed cross-coupling of aryl fluorides.
- Tobisu, Mamoru,Xu, Tian,Shimasaki, Toshiaki,Chatani, Naoto
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supporting information; experimental part
p. 19505 - 19511
(2012/01/31)
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