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Palau’chlor: A Practical and Reactive Chlorinating Reagent

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posted on 17.12.2015, 02:07 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.