Journal
ORGANIC LETTERS
Volume 18, Issue 4, Pages 788-791Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00055
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Funding
- Gobierno Vasco (ELKARTEK-15_Frontiers)
- Universidad del Pais Vasco UPV/EHU [GIU15/31]
- Gobierno Vasco [POS_2015_2-0048]
- UPV/EHU
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4-Alkynyl-1,2,3-triazolium cations undergo thermal [3 + 2] cycloaddition reactions with azides roughly 50- to 100-fold faster than comparable noncharged alkynes. Further, the reaction is highly 1,4-regioselective (dr up to 99:1) owing to the selective stabilization of 1,4-TS transition states via conjugative pi-acceptor :assistance of the alkyne triazolium ring. The novel cationic triazolium alkynes also accelerate the CuAAC reaction to provide bis(1,2,3-triazoles) in an ultrafast way (<5 min).
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