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13.13.6.1.1.1.1 Copper-Catalyzed Cycloadditions

DOI: 10.1055/sos-SD-113-00177

Tomé, A. C.Science of Synthesis Knowledge Updates, (2015260.

The copper(I)-catalyzed azide–alkyne cycloaddition, reported independently in 2002 by the groups of Meldal[‌2‌] and Fokin and Sharpless,[‌3‌] has rapidly become the method of choice to synthesize 1,4-disubstituted 1,2,3-triazoles. The reasons for the success of this “click” reaction include the simplicity and mild conditions of the experiments, the tolerance of a variety of functional groups in both reagents, the regioselectivity, and the high yields of the expected 1,2,3-triazoles. Due to its synthetic versatility and utility, the copper(I)-catalyzed azide–alkyne cycloaddition is considered the “jewel in the crown” of the click reactions.

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Meeeee 8 Meeeeeeeeee ee 8,8-Meeeeeeeeeeee 8-Meee-8,8,8-eeeeeeeee[‌888‌]

Meeeeeeeeee 8

M8 M8 M Meeee (%) Mee
Me Me M 88 [‌888‌]
Me 8-Mee M 88 [‌888‌]
Me 8-MM8M8 M 88 [‌888‌]
Me MMM M 88 [‌888‌]
(MM8)8Me Me M 88 [‌888‌]
(MM8)8Me (MM8)8Me M 88 [‌888‌]
Me M 88 [‌888‌]
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8-MeMM8M8 Me M 88 [‌888‌]
8-MeMM8M8 Me Me 88 [‌888‌]
8-MeMM8M8 8-MeMM8M8 Me 88 [‌888‌]
Me Me 88 [‌888‌]
8-MM8M8 M 88 [‌888‌]

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Meeeeeeeeeee Meeeeeeee

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References


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