Hypervalent iodine promoted ortho diversification: 2-aryl benzimidazole, quinazoline and imidazopyridine as directing templates.,Organic & Biomolecular Chemistry

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Hypervalent iodine promoted ortho diversification: 2-aryl benzimidazole, quinazoline and imidazopyridine as directing templates.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-01-10 , DOI: 10.1039/c9ob02533b
Moumita Saha ₁ , Asish R Das ₁

Affiliation

The mild and efficient palladium-catalyzed ortho C(sp2)-H diversification of (NH)-free 2-substituted benzimidazole, quinazoline, and imidazopyridine is reported using hypervalent iodine as the key reagent. Acetoxy, aryl, iodide and nitro functional groups were introduced on the same substrate by simply shifting the reaction conditions in the presence of inorganic additives (Cs2CO3, I2, NaNO2) and the hypervalent iodine reagent (diacetoxyiodo)benzene (PIDA) under aerobic conditions. The combination of NaNO2 with PIDA was successfully employed in Pd-catalyzed C-H bond nitration to achieve a library of nitrated 1,3 N-heterocycles. This versatile ortho C(sp2)-H activation strategy features operational simplicity, short reaction times, and ample substrate possibilities, it requires no ligands or silver salts as additives, and it shows good tolerance of oxidation prone functional groups.

中文翻译：

高价碘促进邻位多样化：以2-芳基苯并咪唑，喹唑啉和咪唑并吡啶为指导模板。

使用高价碘作为关键试剂，报道了温和而有效的钯催化的不含（NH）2取代的苯并咪唑，喹唑啉和咪唑并吡啶的邻位C（sp2）-H多样化。在有氧条件下，只需在无机添加剂（Cs2CO3，I2，NaNO2）和高价碘试剂（二乙酰氧基碘）苯（PIDA）存在下简单地改变反应条件，即可将乙酰氧基，芳基，碘化物和硝基官能团引入同一底物。NaNO2与PIDA的组合已成功用于Pd催化的CH键硝化反应，从而获得了硝化的1,3 N-杂环文库。这种通用的邻位C（sp2）-H活化策略具有操作简便，反应时间短和底物丰富的可能性，不需要配体或银盐作为添加剂，

更新日期：2020-02-13

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