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Metal‐Free, N ‐Iodosuccinimide‐Induced Regioselective Iodophosphoryloxylation of Alkenes with P(O)−OH Bonds
Author(s) -
Xiong Biquan,
Xu Shipan,
Zhu Yu,
Yao Lei,
Zhou Congshan,
Liu Yu,
Tang KeWen,
Wong WaiYeung
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000575
Subject(s) - regioselectivity , reagent , chemistry , halogenation , phosphoric acid , functional group , combinatorial chemistry , organic chemistry , transition metal , medicinal chemistry , catalysis , polymer
A simple and efficient method for the regioselective iodophosphoryloxylation of alkenes with P(O)−OH bonds has been established by using NIS ( N ‐iodosuccinimide) as the iodination reagent under transition‐metal‐free conditions. The present protocol is compatible with different functional groups, and suitable for various alkenes and P(O)−OH compounds. A variety of functionalized β‐iodo‐1‐ethyl phosphinic/phosphoric acid esters are obtained in good to excellent yields, which could be further transformed to diversified building blocks for the synthesis of bioactive compounds, pharmaceuticals and functional materials.