Photochemical functionalization of diazines: metal-free vinylation and phosphonylation

被引：5

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

共 50 条

[21] Metal-free deprotonative functionalization of heteroaromatics using organic superbase catalyst
Hirono, Yutaro
Kobayashi, Koji
Yonemoto, Misato
Kondo, Yoshinori
CHEMICAL COMMUNICATIONS, 2010, 46 (40) : 7623 - 7624
[22] Metal-Free Functionalization of Azine N-Oxides with Electrophilic Reagents
Sergey V. Baykov
Vadim P. Boyarskiy
Chemistry of Heterocyclic Compounds, 2020, 56 : 814 - 823
[23] Transition Metal-Free ipso-Functionalization of Arylboronic Acids and Derivatives
Zhu, Chen
Falck, John R.
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) : 2395 - 2410
[24] Metal-free functionalization of azine N-oxides with electrophilic reagents
Baykov, Sergey, V
Boyarskiy, Vadim P.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (07) : 814 - 823
[25] Metal-free photochemical silylations and transfer hydrogenations of benzenoid hydrocarbons and graphene
Papadakis, Raffaello
Li, Hu
Bergman, Joakim
Lundstedt, Anna
Jorner, Kjell
Ayub, Rabia
Haldar, Soumyajyoti
Jahn, Burkhard O.
Denisova, Aleksandra
Zietz, Burkhard
Lindh, Roland
Sanyal, Biplab
Grennberg, Helena
Leifer, Klaus
Ottosson, Henrik
NATURE COMMUNICATIONS, 2016, 7
[26] Computational study on the mechanism of metal-free photochemical borylation of aryl halides
Tu, Chenhao
Ma, Nana
Xu, Qingli
Guo, Wenyue
Zhou, Lanxin
Zhang, Guisheng
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2022, 122 (15)
[27] Metal-free photochemical silylations and transfer hydrogenations of benzenoid hydrocarbons and graphene
Raffaello Papadakis
Hu Li
Joakim Bergman
Anna Lundstedt
Kjell Jorner
Rabia Ayub
Soumyajyoti Haldar
Burkhard O. Jahn
Aleksandra Denisova
Burkhard Zietz
Roland Lindh
Biplab Sanyal
Helena Grennberg
Klaus Leifer
Henrik Ottosson
Nature Communications, 7
[28] Oxidizing agents in metal-catalyzed and metal-free C-H functionalization of heteroarenes
Utepova, Irina A.
Chupakhin, Oleg N.
Trestsova, Maria A.
Musikhina, Alexandra A.
Shchepochkin, Alexandr V.
Zabelina, Olga N.
ARKIVOC, 2021, : 240 - 299
[29] Hypervalent Iodine Compounds Mediated Metal-Free C-H Functionalization
Chen, Chunhua
Mo, Dongliang
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (09) : 3012 - 3014
[30] Metal-Free Functionalization of Linear Polyurethanes by Thiol-Maleimide Coupling Reactions
Billiet, Leen
Gok, Ozgul
Dove, Andrew P.
Sanyal, Amitav
Nguyen, Le-Thu T.
Du Prez, Filip E.
MACROMOLECULES, 2011, 44 (20) : 7874 - 7878

← 1 2 3 4 5 →