DDQ-promoted C(sp3)H phosphorylation of cycloheptatriene

[Display omitted] •The DDQ-promoted C(sp3)H phosphorylation has been achieved.•The reactions afford cyclohepta-2,4,6-trien-1-ylphosphonates under mild conditions.•The protocol is halogen-, metal-, and strong base-free. An efficient and convenient C(sp3)H phosphorylation has been achieved via the DDQ...

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Bibliographic Details
Published in:Tetrahedron letters 2019-05, Vol.60 (19), p.1345-1348
Main Authors: Wen, Chunxiao, Yu, Guodian, Ou, Yingcong, Wang, Xiaofeng, Zhang, Kun, Chen, Qian
Format: Article
Language:English
Subjects:
C(sp3)[sbnd]H
Cycloheptatriene
Phosphorylation
Tropylium
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Summary:[Display omitted] •The DDQ-promoted C(sp3)H phosphorylation has been achieved.•The reactions afford cyclohepta-2,4,6-trien-1-ylphosphonates under mild conditions.•The protocol is halogen-, metal-, and strong base-free. An efficient and convenient C(sp3)H phosphorylation has been achieved via the DDQ-promoted cross-dehydrogenative coupling between cycloheptatriene and P(O)H compounds at room temperature. This transformation provides a direct synthetic route to the construction of C(sp3)P bonds with good functional group compatibility, leading to the formation of cyclohepta-2,4,6-trien-1-ylphosphonates in up to 99% yield.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.04.021