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Pd(0)-Catalyzed Cyclizative Phosphorylation of (Z)-1-Iodo-1,6-diene: Synthesis of Alkylphosphonate and Alkylthionophosphonate

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journal contribution
posted on 08.07.2019, 00:00 by Yang Hong, Wei Liu, Ming Dong, Xin Chen, Tong Xu, Ping Tian, Xiaofeng Tong
A palladium-catalyzed cyclizative phosphorylation reaction of (Z)-1-iodo-1,6-diene with diethyl H-phosphonate is developed, which provides facile access to unsaturated six-membered heterocycles bearing an alkylphosphonate group. The key step of this process is the efficient capture of the involved alkyl-Pd­(II) species by H-phosphonate with the help of CsF, followed by reductive elimination of alkyl-Pd­(II)-P­(O)­(OEt)2. Moreover, this reaction is successfully extended to H-thionophosphonate.