Readily Removable Directing Group Assisted Chemo- and Regioselective C(sp(3))-H Activation by Palladium Catalysis.
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 C-H 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.
Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing, 100871 (China).
Yun-Fei
YF
Zhang
College of Chemistry and Chemical Engineering, Shanxi University, Shanxi, 030006 (China).
Hong-Wei
HW
Zhao
Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing, 100871 (China).
Hui
H
Wang
Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing, 100871 (China).
Jiang-Bo
JB
Wei
Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing, 100871 (China).|State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China).
Zhang-Jie
ZJ
Shi
CH activation; arenes; palladium; silver; synthetic methods