Development and application of novel bond formation reactions of heteroaromatic compounds via iodonium intermediates.

联芳基化合物在天然产物、药物、农药和π共轭有机材料的合成中是用途广泛的结构单元。因此，发展简便的偶联反应合成联芳基化合物是有机化学中的重要课题之一。本人通过二芳基碘鎓盐的偶联反应合成了多种杂联芳基化合物。此外，我们还发展了一种不含金属的高价碘试剂区域选择性氧化合成头-尾（H-T）联噻吩的方法。这种独特的不对称偶联反应是通过碘鎓中间体实现的，用于3-取代噻吩的切换反应性，以及中性3-取代噻吩在2-位的排他性亲核性。

Biaryl compounds are versatile building blocks in the synthesis of natural products, pharmaceuticals, agricultural chemicals and π-conjugated organic materials. Therefore, the development of convenient cross-coupling reaction for giving biaryls is one of the important subjects in organic chemistry.I have developed the biaryl cross-coupling reaction of heteroaromatic compounds via diaryl iodonium salts, leading to various heterobiaryls. In addition, we also developed a metal-free regioselective oxidative synthesis of head-to-tail (H-T) bithiophenes using hypervalent iodine (III) reagent. This unique unsymmetrical coupling reaction was realized through the iodonium intermediate for the switching reactivity of 3-substituted thiophenes, and exclusive nucleophilicity of the neutral 3-substituted thiophenes at the 2-position.