0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via 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.

Meeeee(M)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeeee eee eeee eeeeee eee eee ee eeeeeee eee ee eeeeeee ee eeeeeee eeeeeeee, ee ee eeeee, eeeee ee eeee eeeeee eee eeeeeeeeeee eeeeeeeeeeee.[‌88‌,‌88‌,‌88‌] Meee eeeeeeee eeeee eeeeeee-eeee eeeeeeeeee[‌88‌‌88‌] ee ee eeeeeeeeeeee eeeeeeee (eeeeeeeeeeeee eeeeee eeeeeee,[‌88‌] eeeeee eeeeeee,[‌88‌] ee eeeee eeeeeee[‌88‌‌88‌]) eeee eeee eeee eeeeeeee. Meeeeeeee eeeeeee ee eee eeeeee(M) eeeeeeee eeee eeee eeee (eee e eeeeeeeeeeeee eeee ee eee eeeeeee eeeeeeeee eee eeeeeeeeee eeee eee eee[‌88‌]), eee eee eeeeee eeeeeeeeeee eeee ee eee eeeeeeee eeeee [eeeeee(M) eeeeee[‌8‌] eee eeeeee(MM) eeeeeee/eeeeee eeeeeeeee[‌8‌]] eee eeeee eee eeee eeeeee eeee. Mee eeeeee(MM) eeeeeee/eeeeee eeeeeeeee eeeeee ee eeeeeeeeeeee eeeeeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeee eeeeee(M) eeeeeee ee eeeeeeeee ee eeee (ee eeeeeeeee ee eee Me8+) eee eee eeeeeeee ee eee eeeeeeee eeeee eeeeeeee eee eeeeeeeee ee eee. Mee eeeeeeee ee eeeeee ee eeeeee-eeeeeee eeeeeee, eeeee eeee eeeeeee eeeeee(M) eeee eeeeeeeee eee eeeeeeeeeeeeeeeeee, eeeeeee eeeeeeee eee eeee ee eee eeeeee(M)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeeee. Meee[(8-eeeeee-8M-8,8,8-eeeeeee-8-ee)­eeeeee]eeeee (8),[‌88‌] eee eeee-eeeee eeeeeeee 8,[‌88‌] eeeeeeeeeeeee 8,[‌88‌] eee eee eeeeeeeeeeeeeeeeeeeeeeeeeeeee eeee eeee 8[‌88‌] (Meeeee 8) eee eeeeeeee eeee eeeeeee, eee eeeeee eeeeee eeee ee 8,8-eeeeeeeeeeeeeeee, eeeeeeeeeeeee, M,M-eeeeeeeeeeeeeeeeeeeee, M,M,M′-eeeeeeeeeeeeeeeeeeeeeeee, eee eeeee eeeeeeeee eeeeee eee ee eeee. Meeeeee eeee(eeeeeeeee)eeeee eeeeeeeeeee ee eeee 8/8 eeee eeee eeeee eeeeeee ee eeeeeeeeee eee eeeeeeeee.[‌88‌‌88‌] Meeeee(M) eeeeeeeee ee eeee(eeeeeeeee)eeeee 8[‌88‌] eee eeee(eeeeeeeee)eeeeeeee[‌88‌] eee eeeeeeeeeee eeeeeeeee eee eeeeee(M)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeeee.

Meeeee 8 Meeee Meeeeee Meeeeeeeee Meee ee Meeeee(M)-Meeeeeeee Meeee–Meeeee Meeeeeeeeeeee Meeeeeeee[‌88‌]

Mee eeeee ee Meee eee Me eeeeeeee eeee eeeeeeeeee eeeee eee eeee eeeeee eeeeeeeee eeeeeeeee ee eeeeee(M)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeeee. Meeeee eeeeeeeeeeee eeeeee ee 8,8-eeeeeeeeeeeee eeeeeeeee eee eeeeeeee ee 8 ee 8 eeeeeee, ee eeee eeeeeeeeeee, eeeee eee eeeeeeeee eeeeee eeeeee(MM) eeeeeee (8.88 eeee)/eeeeee eeeeeeeee (8.88 eeee) eee e eeeeeeeeee eeee (8.8 eeee) ee eeee-eeeee eeeeeee/eeeee (8:8 e/e), eeee eee eeee eeeeeee eeeee eeeeeeee eeee eeeeeee eeee.[‌88‌] Mee eeee eeeee eeeeeeee ee eeeeeeee eeeeeeeee ee eeee eeeeeeeee 8 eeeeeeeee ee eeee–eeee eeeeeee eeeeeeee eeeeee(M)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeee (Meeeee 8).[‌88‌] Meeeeeeee eeeeeee eeee eeeeeeee eeee eeeeee(M) eeeeee (8.88 eeeee)/M,M-eeeeeeeeeeeeeeeeeeeee (8.88 eeeee)/eeeeee eeee (8.88 eeeee) ee eeeeeeeeeeeeeee, ee eeee eeeeeeeeeee, eee 8 eeeeeee. M eeeeeeeee eeeeee eeeee ee eeeeeeeeeeee eeeeeeeee eeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeee(M) [MeMe(MMe8)8] ee eeee eeeeeeeee ee eeee eeeeeeeeeee, eeee 8.8 eee% ee eeeeee eeeeeeee (ee eeee), ee eee eeeeeee ee eee eeeeeeee. Meee eeeeeeeee eee eeeeeeee eeeeeee eee eeeeeeeeeeee eeee.[‌88‌]

Meeeee 8 Meeeeeeeeee ee 8,8-Meeeeeeeeeeee 8,8,8-Meeeeeeee eee Meeeee(M)-Meeeeeeee Meeee–Meeeee Meeeeeeeeeeee Meeeeeeee[‌88‌]

Meeeee(MM) eeeee eeeeee eeeeeee, eeeeeeee ee eeeeee ee eeeeeee eeeeeee eeeeeeee ee eeeeee(M) eeeee eeeeeeee eeeeeeeee eeeeeeeee, eeee eeeeeee eeeeeeeee eeeeeeeee eeeeeeee ee eeeeee(M)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeeee.[‌88‌]

Meeeeee eeeeee(MM) eeeeeeeee eee eeeeeeeee eeeeeeeeeeee eeeeeee eee eeeeeeeee ee e eeeeeeeeeee eeeeeeeee eeee ee eeeeee eeeeeeeee.[‌88‌‌888‌] Me eeee eeeeeee, eee eeeeee(MM) eeee eee eeeeeeee eeeeeee ee eee eeeeee eeeeee(M) eeeeeeee eeeeeee eee eeeeeeeee eeeeeeeeeeee ee eeeeeee (Meeeee eeeeeeee) ee eeeeeeeee ee eee eeeeeee. Meeeeeee, eeeeeee eeeeeeeee eeeeeeeee eeeee-eeeeeee eeeeee(M)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeeee eeee eeee eeeeeeee.[‌888‌‌888‌] Me eeeee eeeeeeeee, eee eeeeeeee eeeeee(M) eeeeeee ee eeeeeeeee ee eeee ee eeeeeeeeeeeeee ee e eeeeee(MM) eeeeeeeeeee. Meeee eeee ee eeeeeeeee eee eeeeeeeeeeee eeeeeeeee eeeeeee eeee eee ee eeeeeeeeee eeeeeeeeee (eee eeeeeeeeee eeeee eeee eee ee eeeeee ee eee eee ee eeeeeee) eee eee ee eeeeeee ee eeeeee eeeeeeee eee eeee eee eeeeeeee eeeeeee, eeeee eeeee ee eee eeeeeeeee ee eee eeeeee(M) eeeeeee ee eeeeeeeee eeeeee.[‌888‌]

Meeeee(M)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeeee eee eeeeee (eee eeeeee eeeeeeeeeee) eeeeeeee ee eeeee eeeeeeeee eeeeeeee eeeeeee eee eee eeeeeeeeee eeeeee ee eeeeee(M) eeeeeeeee ee eeeeeeeeeeeeee eeeeeeeee ee eeeeee eeee eeeeeeee eeeeeee eee eeee eeee eeeeeeeee.[‌888‌,‌888‌]

Meeeee(M)-eeeeeeeee eeeeeeeee ee eeeeee eeee 8-eeeeeeee-8-eeee[‌888‌] ee 8-eeeeeee-8-eeee[‌888‌,‌888‌] eeee eeeeee ee eee eeeeeeeeeeeee 8,8-eeeeeeeeeeeee 8-eeee-8,8,8-eeeeeeeee. M eeeeee eeeeeeeee eeeeeeee eee 8,8-eeeeeeeeeeeee 8-eeee-8,8,8-eeeeeeeee 8 eeeeeeee e eee-eee eeeeeeee ee e eeeeeeee eeeeee, ee eeeeeee eeeee, eee eeeeee(M) eeeeee ee eeeeee(M) eeeeeee ee eee eeeeeeee ee eeee-eeeeeeeeeeeeeeeeee eeeeeeee (8.8 eeeee) (Meeeee 8).[‌888‌] Mee eeeeeeeee eee eeeeeee eee ee eeee eeeeeeeeeee eeeee ee eeeeee eeeeeeeeee. Mee eeeeeeeee ee eeeee eeeeeeeee eeeeeeee eee eeee-eeeeeeeeeeeeeeeeee eeeeeeee eeeeeeeee eeeeeee eeeeeeeee ee MeM ee M8 eee eee eeeeeeeeeeee ee eee eeeeeeeeeeee (8,8,8-eeeeeee-8-ee)eeeeee eeeeeee. Meeeeeeeeee eeeeeeeee ee eeeeee 8,8-eeeeeeeeeeeee 8-eeee-8,8,8-eeeeeeeee eeeeeee e eeeeeeeeeeeeee eee-eee eeeeeeee ee eeeeee eee eeeeeeee eeeeeee eeeeeeee ee eeeeee(M) eeeeee/eeeeee eeeeeeeeeeee,[‌888‌] ee eeeeee(M) eeeeee/M-eeeeeeeeeeeeeeee,[‌888‌] eeeeee(M) eeeeee eeeeeeee eeeeeeeeeeeeee eeeeeee eeeeee eee eeeeeeee eeeeeee ee eee eeeeeeee ee 8-(eeeeeeeeeeeee)eeeeeeee,[‌888‌] ee eeeeee(MM) eeeeeeeeeee eee eeeeee eeeeee eeeeeeee eeeeeeeeeeeee eeeeeeeee ee eeeeeee eeeeee eee eeeeeeee eeeeeee.[‌888‌]

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]
Me M 88 [‌888‌]
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]

8-Meee-8,8,8-eeeeeeee-eeeeeeeeee eeeeeeeeeee eee ee eeeeeeee ee eeeeeeeeeeeeee eeeeee(M)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeeee ee e eeee eeeeeee eeeee eeeeee eeeeee ee eee eeeeeeee eeeeee[‌888‌,‌888‌] eee eeee(8-eeee-8,8,8-eeeeeeee)e eee eeeeeeeee eee eeee-eeeeee eeeeee(M)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeeeeeeeee ee α-eeeee-ω-eeeeeeeeee eeeeeeee eeeee e eeeeee(M) eeeeee/eeee[(8-eeee-eeeee-8M-8,8,8-eeeeeee-8-ee)eeeeee]eeeee (8) eeeeeeee eeeeee. Mee eeeeeeeeeeeeee eeeeeeee eeeeeeee eeeeeeeeee eeee, eeee eeee-eeeeeeeee-eeeeee eeeeeee eeeeeeee eeeeee 8 eeee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-eeeeee-8M-8,8,8-eeeeeeee (8, M8 = Me; M8 = Me):[‌88‌]

Me e eeeeeee ee MeM (8.8 ee, 8.88 eeee), eMe8MMe (8.8 ee, 8.88 eeee), eee MeMM (8.8 ee, 8.88 eeee) ee MM8Me8 (8.8 eM) eee eeeee e eeeeeee ee eeeeeeeeeeeeeee (888 ee, 8 eeee) eee eeeeee eeeee (888 ee, 8.88 eeee) ee ee. Mee eeeeeeeee eeeeeee eee eeeeeee eeeee eee eeeeee eee eeeeeeeeeee (ee.88 eee). Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee eeee e eeeee eeeeee [eeeeee eee, MeMMe/eeeeeeeee eeeee (ee 88–88 °M) 8:8] ee eeee eee eeeeeee ee ee eee-eeeee eeeee; eeeee: 888 ee (88%).