Journal
ORGANIC LETTERS
Volume 20, Issue 11, Pages 3245-3249Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01105
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Funding
- National Natural Science Foundation of China [21471134, 21571158, 21701148]
- Program for Science & Technology Innovative Research Team in University of Henan Province [15IRTSTHN-002]
- Universities in Henan Province [17A150053]
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The catalytic [5 + 1] annulation/5-exocyclization reaction of amidines with diynes is reported herein. This protocol provides highly atom-economical access to fabricate two nitrogen-containing heterocycles in one step with high efficiency and selectivity. Significantly, this reaction represents the first example of using diyne as a one-carbon reaction partner in C-H functionalization. Kinetic isotope effects suggested that the catalytic cycle of this reaction is initiated by the cleavage of the ortho C-H bond in the N-phenyl ring of amidines, which is likely involved in the rate-limiting step. Calculations based on density functional theory (DFT) indicated that C-H activation and the formation of Rh(V) species via 5-exo-cyclization could be vital processes for this cascade transformation.
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