A simple base-mediated halogenation of acidic sp2 C-H bonds under noncryogenic conditions.
A new method has been developed for in situ halogenation of acidic sp(2) carbon-hydrogen bonds in heterocycles and electron-deficient arenes. Either selective monohalogenation or one-step exhaustive polyhalogenation is possible for substrates possessing several C-H bonds that are flanked by electron-withdrawing groups. For the most acidic arenes, such as pentafluorobenzene, K(3)PO(4) base can be employed instead of BuLi for metalation/halogenation sequences.
Do
Hien-Quang
HQ
Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA.
Daugulis
Olafs
O
D002244:Carbon / Q000737:chemistry*; D004583:Electrons; D054879:Halogenation; D006571:Heterocyclic Compounds / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry*; D013696:Temperature
D006571:Heterocyclic Compounds; D002244:Carbon; D006859:Hydrogen