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Synthesis of C2‐Phosphorylated Indoles via Metal‐Free 1,2‐Phosphorylation of 3‐Indolylmethanols with P(O)‐H Species
Author(s) -
Zou YunXiang,
Liu XiaoYan,
Zhang Jing,
Yang HongLi,
Yang XinYue,
Liu XiaoLing,
Chu YiWen,
Chen Long
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900987
Subject(s) - chemistry , phosphorylation , amide , phosphine , metal , stereochemistry , substrate (aquarium) , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , biochemistry , oceanography , geology
An efficient and practical method for synthesis of C2‐phosphorylated indoles has been disclosed via a metal‐free 1,2‐phosphorylation of 3‐indolylmethanols with H ‐phosphine oxides or H ‐phosphonates. This alternative protocol features a broad substrate scope with respect to both 3‐indolylmethanols derived from isatins, acyclic α‐keto amide, α‐keto ester, 1,2‐diketone and simple ketones and H ‐phosphine oxides or H ‐phosphonates, moderate to high yields and mild reaction conditions. Mechanistic studies indicate that this reaction proceeds via an unusual direct 1,2‐addition pathway, in which the existence of an electron‐withdrawing group adjacent to the hydroxyl group of 3‐indolylmethanols plays a decisive role.