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Palau'chlor: a practical and reactive chlorinating reagent.

ABSTRACT: 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.

SUBMITTER: Rodriguez RA

PROVIDER: S-EPMC4333596 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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Palau'chlor: a practical and reactive chlorinating reagent.

Rodriguez Rodrigo A RA Pan Chung-Mao CM Yabe Yuki Y Kawamata Yu Y Eastgate Martin D MD Baran Phil S PS

Journal of the American Chemical Society 20140429 19

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 ...[more]

PMID: 24758725

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