Photochemical functionalization of diazines: metal-free vinylation and phosphonylation

被引：6

作者：

Erbland, Guillaume ^{[1
]}

Ruch, Jonas ^{[1
]}

Goddard, Jean-Philippe ^{[1
]}

机构：

[1] Univ Haute Alsace, Lab Chim Organ & Bioorgan EA 4566, Ecole Natl Super Chim Mulhouse, 3 Bis Rue Alfred Werner, F-68093 Mulhouse, France

来源：

TETRAHEDRON | 2016年 / 72卷 / 48期

关键词：

Photochemistry; Diazines; Radical chemistry; Photo-Arbuzov reaction; Diazinyl phosphonate; VISIBLE-LIGHT PHOTOCATALYSIS; PHOTOREDOX CATALYSIS; ARBUZOV REACTION; ARYL; HETEROARENES; REACTIVITY; VINYLPHOSPHONATE; PHOTOLYSIS; CHEMISTRY; PHOSPHITE;

D O I：

10.1016/j.tet.2016.07.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under mild UVA irradiation, the C-Br bond of bromodiazines can be activated to generate the corresponding radical intermediate. In the presence of alkynes, alkenylation reactions occurred to afford vinyl pyrimidine in moderate yields. Csp2-phosphorous bond can also be easily created in a photochemical version of the Arbuzov reaction. With UVA and a stoichiometric amount of trimethyl phosphite, the corresponding phosphonates were isolated in good to high yields. Very interesting selectivities were observed under these mild irradiation conditions. Functionalized substrates can be engaged and the resulting products could be further derivatized. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：7826 / 7831

页数：6

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