Highly Efficient Aerobic Oxidative Hydroxylation of Arylboronic Acids: Photoredox Catalysis Using Visible Light
Highly Efficient Aerobic Oxidative Hydroxylation of Arylboronic Acids: Photoredox Catalysis Using Visible Light
复制标题
芳基硼酸的高效有氧氧化羟基化：使用可见光的光氧化还原催化
DOI：
10.1002/anie.201107028
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发表时间：
2012-01-01
影响因子：
16.6
通讯作者：
Xiao, Wen-Jing
中科院分区：
文献类型：
--
作者：
Zou, You-Quan;Chen, Jia-Rong;Xiao, Wen-Jing
开发有效合成精细化学品的绿色和可持续方法是我们社会的一个重要目标。在过去的十年中，可见光光氧化还原催化作为推进这些目标的方法显示出巨大的前景。由于其自然丰度高、环境影响良性、清洁和可持续性，[1]使用可见光的光催化是一种可靠且强大的工具。[2]在这方面，有几个有用的例子，包括醛的不对称烷基化、烯酮的[3][2+2]环加成、芳基环丙基酮的[4][3+2]环加成、[5]还原脱卤、[3d, 6]不饱和键的自由基加成、[7]和偶联反应。 [8, 9] 这些进展中，由可见光引发的氧化反应在很大程度上尚未被探索。 2003 年，Zen 等人。报道了将硫化物氧化成亚砜的可见光光催化反应。 [10]后来，赵等人。使用可见光和染料敏化 TiO2 将醇氧化为醛。[11]最近，Blechert和Wang[12]团队开发了一种无金属光氧化系统来实现胺和醇的氧化，Jiao等人。描述了使用RuII聚吡啶络合物和4-甲氧基吡啶促进α-芳基卤素衍生物转化为α-芳基羰基化合物。[13]空气中的分子氧已广泛用作合成中的绿色氧化剂。[14]因此，非常需要开发使用空气作为氧化剂的可见光光氧化反应。我们最近开发了一种可见光诱导的氧化/[3+2]环加成/氧化芳构化序列，用于二氢异喹啉酯和缺电子烯烃或炔烃构建吡咯并[2, 1-a]异喹啉。 [15, 16] 在该序列中，超氧自由基阴离子，
The development of green and sustainable methods for effective synthesis of fine chemicals is an important goal in our society. During the last decade, visible-light photoredox catalysis has shown great promise as a method to advance these goals. As a result of its high natural abundance, benign environmental impact, cleanliness, and sustainability,[1] photocatalysis using visible light is a reliable and powerful tool.[2] In this context, there are several examples of its usefulness, including asymmetric alkylation of aldehydes,[3][2+ 2] cycloaddition of enones,[4][3+ 2] cycloaddition of aryl cyclopropyl ketones,[5] reductive dehalogenation,[3d, 6] radical addition to unsaturated bonds,[7] and coupling reactions.[8, 9] Despite these advances, oxidative reactions initiated by visible light are largely unexplored. In 2003, Zen et al. reported a visible-light photocatalytic reaction for the oxidation of sulfides into sulfoxides.[10] Later, Zhao et al. oxidized alcohols to aldehydes using visible light and dye-sensitized TiO2.[11] Recently, the groups of Blechert and Wang [12] developed a metal-free photooxidative system to achieve the oxidation of amines and alcohols, and Jiao et al. described the use of a RuII polypyridine complex and 4-methoxypyridine to promote the conversion of α-aryl halogen derivatives into α-aryl carbonyl compounds.[13]The molecular oxygen in air has been widely used as a green oxidant in synthesis.[14] Consequently, the development of visible-light photooxidative reactions using air as the oxidant is highly desirable. We recently developed a visiblelight-induced oxidation/[3+ 2] cycloaddition/oxidative aromatization sequence for dihydroisoquinoline esters and electrondeficient alkenes or alkynes to construct pyrrolo [2, 1-a] isoquinolines.[15, 16] In this sequence, a superoxide radical anion,