Chiral acid-catalysed enantioselective C−H functionalization of toluene and its derivatives driven by visible light

Fuyuan Li, Dong Tian, Yifan Fan, Richmond Lee, Gang Lu, Yanli Yin, Baokun Qiao, Xiaowei Zhao, Ziwei Xiao and Zhiyong Jiang ()
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Fuyuan Li: Henan University
Dong Tian: Henan University
Yifan Fan: Henan University
Richmond Lee: Singapore University of Technology and Design
Gang Lu: Shandong University
Yanli Yin: Henan University
Baokun Qiao: Henan University
Xiaowei Zhao: Henan University
Ziwei Xiao: Henan University
Zhiyong Jiang: Henan University

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract Toluene and its derivatives are petroleum-derived raw materials produced from gasoline by catalytic reformation. These abundant chemical feedstocks are commonly used as solvents in organic synthesis. The C(sp3)−H functionalization of these unactivated substrates has been widely used to directly introduce benzylic motifs into diverse molecules to furnish important compounds. Despite these advances, progress in asymmetric catalysis remains underdeveloped. Here, we report photoinduced radical-based enantioselective C(sp3)−C(sp3) coupling reactions of activated ketones with toluene and its derivatives by means of chiral acid catalysis. With a La(OTf)3/pybox complex catalyst, a variety of chiral 3-hydroxy-3-benzyl-substituted 2-oxindoles, including many conventionally difficult-to-access variants, are obtained directly from isatins in high yields with good to excellent enantioselectivities. Acenaphthoquinone is also compatible with the use of a chiral phosphoric acid (CPA) catalyst, leading to another series of important enantioenriched tertiary alcohols.

Date: 2019
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DOI: 10.1038/s41467-019-09857-9

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