Phosphorylation of C(sp3)–H Bonds via 1,4-Palladium Migration

1,4-Palladium migration has emerged as a reliable method for directed C–H functionalization. In contrast to coupling with carbon nucleophiles, limited examples with heteroatom nucleophiles have been reported. Herein we report a palladium-catalyzed intermolecular C­(sp3)–H phosphorylation reaction vi...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 21; pp. 3781 - 3785
Main Authors Ji, Xiao-Ming, Chen, Yan-Zhen, Fu, Jian-Guo, Zhang, Shu-Sheng, Feng, Chen-Guo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.06.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,4-MIGRATION
ARYL
C-H ACTIVATION
BORYLATION
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Summary:1,4-Palladium migration has emerged as a reliable method for directed C–H functionalization. In contrast to coupling with carbon nucleophiles, limited examples with heteroatom nucleophiles have been reported. Herein we report a palladium-catalyzed intermolecular C­(sp3)–H phosphorylation reaction via 1,4-palladium migration, which is often difficult because of the strong coordination of phosphorus reagents to palladium catalysts. Phosphorylation of C­(sp3)–H bonds is accomplished in good reaction yields with excellent regioselectivity. The judicious selection of the phosphine ligand proved to be the key to the success of this cascade process.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01303