American Chemical Society
ja5031744_si_015.cif (385.23 kB)

Palau’chlor: A Practical and Reactive Chlorinating Reagent

Download (385.23 kB)
posted on 2015-12-17, 02:07 authored by Rodrigo A. Rodriguez, Chung-Mao Pan, Yuki Yabe, Yu Kawamata, Martin D. Eastgate, Phil S. Baran
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.