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Visible‐Light Photoredox‐Catalyzed Cross‐Dehydrogenative Coupling of Tetrahydroisoquinolines with 3‐Fluorooxindoles
Author(s) -
Ji Jian,
Chen LingYan,
Qiu ZiBin,
Ren Xinfeng,
Li Ya
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900378
Subject(s) - chemistry , tetrahydroisoquinoline , propargyl , photoredox catalysis , alkyl , aryl , yield (engineering) , catalysis , substrate (aquarium) , combinatorial chemistry , stereochemistry , photochemistry , organic chemistry , photocatalysis , materials science , oceanography , metallurgy , geology
The 3‐fluorooxindole and tetrahydroisoquinoline scaffolds are both important structures because of their associated biological and pharmaceutical activities. Herein, we report a highly diastereoselective synthesis of 3‐fluorooxindoles fully substituted at the 3‐position and containing a tetrahydroisoquinoline fragment, through the visible‐light photoredox‐catalyzed cross‐dehydrogenative coupling of tetrahydroisoquinolines with 3‐fluorooxindoles. The protocol featured a wide substrate scope: N‐alkyl‐, N‐haloalkyl‐, N‐aryl‐, N‐allyl‐, N‐propargyl‐, and NH 3‐fluorooxinloles were all able to be used to form the desired coupling products in up to 92% yield and 99 : 1 anti/syn .
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