二苯并噻吩s -氧化物的能量转移激发诱导苯乙烯的氧甲基化。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-02 DOI:10.1021/acs.orglett.5c03852

Saki Maejima,Ban Kinoshita,Ryota Wakabayashi,Manabu Abe,Hideki Yorimitsu

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引用次数: 0

摘要

亚砜的光激发传统上需要强烈的紫外光照射，从而限制了它们在有机合成中的适用性。在这里，我们报道了在表面- ir (ppy)3催化和蓝光照射下的光敏作用在更温和的条件下有效地激发了二苯并噻吩s -氧化物。受激发的亚砜与DMSO溶剂发生反应，促进苯乙烯的氧甲基化。机理研究表明，受激发的二苯并噻吩s -氧化物在DMSO中快速裂解生成甲基自由基、甲基磺酰基自由基和二苯并噻吩。该工艺提供了一种新的光催化生成甲基自由基的方法，无需求助于过氧化物或金属氧化剂。

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Energy-Transfer Excitation of Dibenzothiophene S-Oxide Induces Oxomethylation of Styrenes.

The photoexcitation of sulfoxides has traditionally required intense UV light irradiation, thereby limiting their applicability in organic synthesis. Here we report that photosensitization under fac-Ir(ppy)3 catalysis and blue-light irradiation effectively excites dibenzothiophene S-oxide under much milder conditions. The excited sulfoxide reacts with DMSO solvent to promote the oxomethylation of styrenes. Mechanistic investigations disclosed that the excited dibenzothiophene S-oxide undergoes rapid fragmentation in DMSO to generate a methyl radical, a methylsulfonyl radical, and dibenzothiophene. This process provides a new photocatalytic method to generate a methyl radical without recourse to peroxides or metal oxidants.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.