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13.13.6.1.1.2 Intramolecular 1,3-Dipolar Cycloadditions

DOI: 10.1055/sos-SD-113-00177

Tomé, A. C.Science of Synthesis Knowledge Updates, (2015276.

Many of the methodologies developed for the intermolecular copper(I)- and ruthenium(II)-catalyzed azide–alkyne cycloadditions have also been successfully used in intramolecular copper(I)- and ruthenium(II)-catalyzed azide–alkyne cycloaddition reactions. Starting from substrates bearing azido and alkyne groups, and using catalyst control, a common intermediate can be converted into two structurally unique macrocycles with either a 1,5- or a 1,4-disubstituted 1,2,3-triazole unit. Depending on the catalyst used, the ring size of the resulting macrocycle is n or n + 1. This concept is clearly demonstrated in the work of Marcaurelle and co-workers (Scheme 15).[‌239‌]

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