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Visible-light TiO2-catalyzed synthesis of dihydrobenzofurans by oxidative [3 + 2] annulation of phenols with alkenyl phenols
Chemical Science ( IF 8.4 ) Pub Date : 2024-03-28 , DOI: 10.1039/d4sc00723a
Jingze Wu 1 , Yaning Liu 1 , Marisa C. Kozlowski 1
Affiliation  

An oxidative strategy for the preparation of dihydrobenzofurans via heterogeneous photocatalysis is reported. This method leverages the surface interaction between the alkenyl phenol and the TiO2 solid surface, which enables direct activation by visible light without the need for pre-functionalization or surface modification. The resulting alkenyl phenoxyl radical is proposed to be selectively captured by a neutral phenol nucleophile, rendering β-5′ coupling with excellent chemo- and regio-selectivity. The reaction proceeds under benign conditions, using an inexpensive, nontoxic, and recyclable photocatalyst under visible light irradiation with air as the terminal oxidant at room temperature.

中文翻译:

可见光 TiO2 催化酚与烯基酚氧化[3+2]成环合成二氢苯并呋喃

报道了通过非均相光催化制备二氢苯并呋喃的氧化策略。该方法利用烯基苯酚和TiO 2固体表面之间的表面相互作用,从而能够通过可见光直接激活,而不需要预功能化或表面改性。由此产生的烯基苯氧基自由基被中性苯酚亲核试剂选择性捕获,使 β-5' 偶联具有优异的化学和区域选择性。该反应在良性条件下进行,使用廉价、无毒且可回收的光催化剂,在可见光照射下,以空气作为终端氧化剂,在室温下进行。
更新日期:2024-03-28
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