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Readily Removable Directing Group Assisted Chemo‐ and Regioselective C(sp 3 )H Activation by Palladium Catalysis
Author(s) -
Zhang YunFei,
Zhao HongWei,
Wang Hui,
Wei JiangBo,
Shi ZhangJie
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201505932
Subject(s) - palladium , chemistry , catalysis , regioselectivity , amide , aryl , selectivity , substrate (aquarium) , reactivity (psychology) , surface modification , combinatorial chemistry , linker , organic chemistry , medicinal chemistry , medicine , alkyl , oceanography , alternative medicine , pathology , computer science , operating system , geology
Currently used directing groups for selective aliphatic β‐functionalization of carbonyl compounds show excellent reactivity and selectivity with an amide as a linker. Described herein is 2‐piconimide, used for the first time with commercially available 2‐picolinamide/2‐picolic acid as precursors, to direct CH arylation/alkenylation by palladium catalysis. The directing group is essential for promoting the sequnetial primary and secondary C(sp 3 )H arylation with different aryl iodides in one substrate. The directing group was easily removed under simple reaction conditions at room temperature.