期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 19, 页码 6908-6911出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja5031744
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资金
- NSF
- JSPS
- NIH/NIGMS [GM-073949]
- Bristol-Myers Squibb
- Sigma-Aldrich
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 pi-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.
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