Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 14, Pages 5031-5034Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b01833
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Funding
- National Science Foundation [CHE-1564959]
- University of Illinois at Chicago
- Office of the Vice Chancellor for Research
- Huaqiao University Xiamen
- Fujian Hundred Talents Plan
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1564959] Funding Source: National Science Foundation
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A new reactivity pattern of Rh-2(II)-Narylnitrenes was discovered that facilitates the synthesis of medium-sized N-heterocycles from ortho-cyclobutanol-substituted aryl azides. The key ring-expansion step of the catalytic cycle is both chemoselective and stereospecific. Our mechanistic experiments implicate the formation of a rhodium N-arylnitrene catalytic intermediate and reveal that spa(3) C-H bond amination of this electrophilic species is competitive with the ring-expansion process.
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