Journal of Organic Chemistry p. 6109 - 6118 (2015)
Update date:2022-07-31
Topics:
Zhou, Yujing
Ye, Fei
Wang, Xi
Xu, Shuai
Zhang, Yan
Wang, Jianbo
An efficient method for the synthesis of organophosphonates through palladium-catalyzed coupling of α-diazo phosphonates with benzyl or allyl halides has been developed. Trisubstituted alkenylphosphonates bearing versatile functional groups can be easily accessed in good yields and with excellent stereoselectivity through this method. Moreover, with similar strategy α-substituted vinylphosphonates can also be attained by the palladium-catalyzed coupling reaction of N-tosylhydrazones and aryl bromides. Migratory insertion of palladium carbene is proposed as the key step in this reaction.
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