Hetaryl Bromides Bearing the SO2F Group - Versatile Substrates for Palladium-Catalyzed C-C Coupling Reactions

被引：17

作者：

Cherepakha, Artem Yu. ^{[1
,2
]}

Stepannikova, Kateryna O. ^{[1
,2
]}

Vashchenko, Bohdan V. ^{[1
,2
]}

Gorichko, Marian V. ^{[2
]}

Tolmachev, Andrey A. ^{[1
,2
]}

Grygorenko, Oleksandr O. ^{[1
,2
]}

机构：

[1] Enamine Ltd, Chervonotkatska St 78, UA-02094 Kiev, Ukraine

[2] Taras Shevchenko Natl Univ Kyiv, Volodymyrska St 60, UA-01601 Kiev, Ukraine

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 47期

关键词：

Sulfur heterocycles; Sulfonyl fluorides; Cross-coupling; Homogeneous catalysis; POTENT ORAL ACTIVITY; DIABETIC-RAT MODELS; NON-CARBOXYLIC ACID; SULFONYL FLUORIDES; ALDOSE REDUCTASE; CROSS-COUPLINGS; NON-HYDANTOIN; INHIBITORS; DERIVATIVES; SERIES;

D O I：

10.1002/ejoc.201801270

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of novel five- and six-membered heteroaromatic sulfonyl fluorides bearing bromine atom at various positions of the heterocyclic ring is described. The synthetic utility of these compounds is demonstrated by the Suzuki, Stille, and Negishi cross-coupling reactions, which proceeded chemoselectively at the aryl bromide moiety with 69-98 % yields. The tolerance of the SO2F group towards the coupling reaction conditions was confirmed in most of the experiments. The proposed method was efficient for either sp(2)-sp(2) or sp(2)-sp(3) C-C couplings. The developed procedure provides rapid access to various substituted heterocyclic sulfonyl fluorides.

引用

页码：6682 / 6692

页数：11

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