Premium
Copper(I)/Bpy‐Catalyzed C‐2‐H Benzylation of Quinazolin‐4(3 H )‐ones with N ‐Tosylhydrazones
Author(s) -
Li Fei,
Gu XiaoJuan,
Zeng ChangE.,
Li Xia,
Liu Bo,
Huang GuoLi
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000244
Subject(s) - chemistry , catalysis , copper , combinatorial chemistry , medicinal chemistry , coupling reaction , reaction mechanism , stereochemistry , organic chemistry
A general and efficient copper‐catalyzed C–H benzylation reaction of quinazolin‐4(3 H )‐ones with N ‐tosylhydrazones is reported. The formation of new C(sp 3 )–C(sp 2 ) bonds through cross‐coupling occurs at the electron‐poor C‐2 position of quinazolin‐4(3 H )‐one and represents an exceedingly practical method to afford 2‐benzylated quinazolin‐4(3 H )‐ones in moderate to good yields under mild reaction conditions. A possible reaction mechanism for this transformation was proposed. This catalytic transformation has the potential to be an important synthetic application for the late‐stage functionalization of advanced synthetic intermediates.