Palau'chlor: a practical and reactive chlorinating reagent.
Unlike its other halogen atom siblings, the utility of chlorinated arenes and (hetero)arenes are twofold: they are useful in tuning electronic structure as well as acting as points for diversification via cross-coupling. Herein we report the invention of a new guanidine-based chlorinating reagent, CBMG or "Palau'chlor", inspired by a key chlorospirocyclization en route to pyrrole imidazole alkaloids. This direct, mild, operationally simple, and safe chlorinating method is compatible with a range of nitrogen-containing heterocycles as well as select classes of arenes, conjugated π-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Rodrigo A
RA
Rodriguez
Chung-Mao
CM
Pan
Yuki
Y
Yabe
Yu
Y
Kawamata
Martin D
MD
Eastgate
Phil S
PS
Baran
D000470:Alkaloids / Q000737:chemistry; D019791:Guanidine / Q000031:analogs & derivatives*; D054879:Halogenation; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D008958:Models, Molecular; D011758:Pyrroles / Q000737:chemistry
D000470:Alkaloids; D006843:Hydrocarbons, Chlorinated; D007093:Imidazoles; D007202:Indicators and Reagents; D011758:Pyrroles; C029899:imidazole; D019791:Guanidine