Science of Synthesis

Forgione, P.; Fader, L. D., Science of Synthesis, (2008) 36, 553.

Zinc has proven to be one of the most well studied and versatile metals in activating terminal alkynes and subsequent reaction with aldehydes and ketones.[‌65‌,‌68‌] Zinc(II) trifluoromethanesulfonate is the most employed activator of the terminal alkyne.

Mee ee eee eeee eeeeee, eee eeeeeeeeeeeee eeeeee, eeeeeee eee eee eeee-eeeeeeee eeeeeeeeeeee eeeeeeee ee eeeeeee eee eeee eeeeeeeee ee Meeeeeee eee ee-eeeeeee (‌Meeeee 88‌).[‌88‌] Meee eeeeeeee eee ee eeeeeeeee eeeee ee eee eeeeeeeeee eeee eeeeeeeeeeee eeeeeee ee eeeeeee eee eeeeeee eeeeee eeeeeeeeeee eeeeeeee ‌88‌ eeee eeeeeeeee ee eeee ee eeeeeeeee eeeeee eee eeee eeee ee eeeeeeeee eeeeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeee eeeeeeeeee ee M-eeeeeeeeeeeeeee (‌88‌). M eeeee eeeeeeeee ee eeee eeeeeeeee ee eeee eee eeee eeeeeeeeee eee ee eeeeeeee ee eeee eeee eeeeeee ‌88‌; eee eeeeeeee eeeeeee eeeeeeeeeee eeee eee eeee ee ee eeeeeeee eeeeeeeeee.

‌Meeeee 88‌ M-Meeeeeeeeeeeeee eee Mee Mee ee Meee-Meeeeeee Meeeeeee ee Meeeeee ee Meeeeeeee[‌88‌]

Me e eeeeeee eeeeeeeeee ee eee eeeeee, Meeeeeee eeeee eeeeee eeee eee eeeeeeee eee ee eeeeeeeee eeeeeeeee eeeeeeeee eeeeeee ee eeee(MM) eeeeeeeeeeeeeeeeeeeeeeeee eee e eeeeee, eeeeeeee eeeeee ee eee eeeeeeeeeee eeee eeeee ee eee eeeeeeee ee eeeeeeeeee.[‌88‌] Me eeeee ee eeee, eee eeeeee eeeeeeeee eeee eee eee eeeeeeee eeee eeeee eeeeeeeee eeeeeeeeee.[‌88‌–‌88‌]

M eeee eeeeeeee eeeeeeeee ee eeee eeee ee eee eeeeeee ee eee eeeeeeeee eeeeee ee eeeeeeeee ee ee eeeeeeeeeeeeeeee eeeeee ee eeeeee eeeeee eeeeeeee eeeeeeeeeee eeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌] Meeeeeee eeeee eeeeeeeee eee eeeeee eeee eee eeeeeeeeeee eeeeeeee, eeee eeeeee eee eeeeeeee eeee eeeeeeee ee eeeeeeeee eeeeeeeee ee eeeeeeeee, eeeeeeee eeee eeeeee eeeeee eee eeeeeeee eee eeee eeeeee eeeeeeee eeeee eee eeeeeeee eeee eeee ee eeeeeee eeeeeeeee.

‌Meeeee 88‌ Meee-Meeeeeee Meeeeeee ee Meeeeeeee ee Meeeeeeee[‌88‌]

Mee eee eeeeee eeee eee eeeeeeee eeee eee eeeeee eeeeeeee ee eeeeeeeee eeeeee eee ee eeeeeeeeeeee ee eee eeeeeeee ee 8-eeeeeeeee-8-ee-8-ee (‌88‌) ee eeeeeeeee (eeeee M8 ee α-eeeeeeee) eee eee eeeee eeeeee, eee eeee eeeeeeee ee eee eeeeeeee eeeeeee ee eeeeeee ‌88‌ ee eeeeeee eee eeeeeee eeeeeeee eeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌] Meee eee ee eeeeeeeee eeee eeee eeee ee eeeeeeeee eeeeee eee e eeeeee ee eeeeeeeeee.

‌Meeeee 88‌ Meee-Meeeeeee Meeeeeee ee 8-Meeeeeeee-8-ee-8-ee ee Meeeeeeee[‌88‌]

Meeee eeeeee eeeeeee eeee eeee eeee eeee eeeeeeeeeeee eeeeeeee eee eeee eeeeeeeeeeeeee, eeeeeeeee eee eeeeeee eeeeeeeeeee eeeeeeee ee eeee eeeeee eeee eeee ee eeeeeeeee eeeeeeeeeeeeeeeeeeee, eeeeeee eeeee eeeeeee,[‌88‌] eeeeeeeeeee,[‌88‌] eeeeeeeeee,[‌88‌] eee eeeeeeeeeee[‌88‌] eeeeeee.

Meeeeee eeeeeeeee ee eeeeeee eee eeee ee eeeeeeeeeeee eeeeeeeee eeeeeeeeeee eeee(MM) eeeeeeee ee eee eeeeeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeee Meeeeeee ‌88‌; Meeeeee Meeeeeeee ee Meee-Meeeeeee Meeeeeee ee Meeeeee ee Meeeeeeee:[‌88‌]

M 88-eM eeeee eee eeeeeee eeee Me(MMe)8 (888 ee, 8.88 eeee) eee (+)-M-eeeeeeeeeeeeeee (‌88M‌; 888 ee, 8.88 eeee) eee eeeeee eeee M8(e) eee 88 eee. Me eee eeeee eee eeeee eeeeeee (8.8 eM) eee Me8M (88 ee, 8.88 eeee). Mee eeeeeeeee eeeeeee eee eeeeeee ee 88°M eee 8 e, eeeeee eee eeeeee ‌88‌ (8.88 eeee) eee eeeee ee eeeeeee ee eee eeeeeee. Meeee 88 eee ee eeeeeeee, eee eeeeeeee (8.88 eeee) eee eeeee ee eeeeeee ee eee eeeeeee. Mee eeeeeee eee eeeeeee eeeee eee eeeeeeee eee eeeeeeee, eeee eeeeeeee ee eeeeeeee ee eee. ee MM8Me (8 eM), eee eeeeee eeee e eeeeeeeeee eeeeee eeeeeeeeee Me8M (88 eM). Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88 eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeeeee ee eeeee eeeeee eeeeeeeeeeeeee eeee eee eeeeeee. Mee eeeeeeeeeeee eeeeee eee eeeeeeeeee ee eeeeee MMMM.

Meeeeeeeeee Meeeeeee ‌88‌; Meeeeee Meeeeeeee ee Meeeeeeee Meee-Meeeeeee Meeeeeee ee Meeeeee ee α-Meeeeeeeeeeeeee Meeeeeeee:[‌88‌]

M 88-eM eeeee eee eeeeeee eeee Me(MMe)8 (88 ee, 8.88 eeee). Meeeee (<8.88 Meee) eee eeeeeee eee eee eeeee eee eeeeee ee 888°M eeeeeeeee. Mee eeeee eee eeeeee ee 88°M, eee eeeeee eee eeeeeeee, eee (+)-M-eeeeeeeeeeeeeee (‌88M‌; 88 ee, 8.88 eeee) eee eeeee. Meeeee (<8.88 Meee) eee eeeeeee eee 8.8 e eee eeee eeeeeeee. Me eee eeeee eee eeeee eeeeeee (8.8 eM) eee Me8M (88 ee, 8.88 eeee). Mee eeeeeeeee eeeeeee eee eeeeeee eee 8 e ee 88°M eee eeee eee eeeeee ‌88‌ (8.88 eeee) eee eeeee ee eee eeeeeee. Meeee eeeeeeee eee 8.88 e ee 88°M, eee eeeeeeee (8.88 eeee) eee eeeee ee eee eeeeeee. Mee eeeeeee eee eeeeeee ee 88°M, eeee eeeeeeee ee eeeeeeee ee eee. ee MM8Me (8 eM), eee eeeeee eeee e eeeeeeeeee eeeeee eeeeeeeeee Me8M (88 eM). Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eee. ee MeMe (88 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee) eeeeeeee eee eeeeeeeee eeeeeee.

Meeeeeeeeee Meeeeeee ‌88‌; Meeeeee Meeeeeeee ee Meeeeeeeeeee Meeeeeee ee Meeeeeeee ee Meeeeeeee:[‌88‌]

M 888-eM eeeee eeeeeeee-eeeeeeee eeee eee eeeeeee eeee Me(MMe)8 (8.88 e, 8.88 eeee), eeeee ee eeeeeeeeee eee eeeeeee eeee e eeee eee, eee eeee eeeeee eeee M8(e). (+)-M-Meeeeeeeeeeeeee (‌88M‌; 888 ee, 8.88 eeee), eeeeeee (88 eM), eee eMe8MMe (8.88 e, 8.8 eeee) eeee eeeee, eee eee eeeeeee eee eeeeeee ee ee eee 8 e eeeee M8. Me eee eeeeeeeee eeeeeeeeee eee eeeee eee eeeeeeee (8.88 eeee). Mee eeeeeee eee eeeeee ee −88°M eee eeeeeeeee eeee eeeeeeeee ee eeeeeeee eee eee eeeeeee eee eeeeeee eee 88 eee eeeeee eee eeeeeee eee eeeeee eeeeeee. Mee eeeeeeeee eeeeeeeeee eee eeeeeee ee ee eee 8±88 e. Mee eeeeeee eee eeeeee ee −88°M eee eeeeee eeeeeeeee. Me eee eeeeeeee eeeeeee eee eeeee eee. ee MM8Me (88 eM) eeeeeeee, eee eee eeeeeee eee eeeeeee ee eeee ee ee eeee eeeeeeee eee 8 e. Mee eee eeeeee eeee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeee eeee eeeee (88 eM) eee eeeee (Me8MM8) ee eeeeee eee eeeee eeeeeee ee e eeee ee eeeeeee.

8-Meeeeeeee-8-ee-8,8-eeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

M 88-eM eeeee eee eeeeeee eeee Me(MMe)8 (888 ee, 8.88 eeee) eee (–)-M-eeeeeeeeeeeeeee (‌88M‌; 888 ee, 8.88 eeee) eee eeeeee eeee M8 (e) eee 88 eee. Me eee eeeee eee eeeee eeeeeee (8.8 eM) eee Me8M (88 ee, 8.88 eeee). Mee eeeeeeeee eeeeeee eee eeeeeee eeeeeeeeee ee 88°M eee 8 e eeeeee eee eeeeee ‌88‌ (88 ee, 8.88 eeee) eee eeeee ee eeeeeee ee eee eeeeeee. Meeee 88 eee ee eeeeeeee, eee eeeeeeee (8.88 eeee) eee eeeee ee eee eeeeeee ee eeeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeeeeee eee eeee eeeeeeee ee eee eeeeeeee ee eee. ee MM8Me (8 eM). Mee eeeeeee eee eeeeee eeee e eeeeeeeeee eeeeee eeeeeeeeee Me8M (88 eM). Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88 eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee) eeeeeeee eee eeeeeee.

Meeeeeeee Meeeeeee Meeeeeeeeee Meeeeeee ‌88‌; Meeeeee Meeeeeeee ee Meeeeeeee ee Meeeeee ‌88‌:[‌88‌]

M 88-eM eeeee eee eeeeeee eeee eeeeee M8MM8 (888 ee, 8.88 eeee) eee 88-eeeee-8 (888 ee, 8.88 eeee) eee eeee eeeeee eeee M8. Me eee eeeee eee eeeee eee eeeeee ‌88‌ (8.88 e, 8.88 eeee) ee eeeeeee (8 eM + 8 eM eeee) eee eee eeeeeeeeee eee eeeeee ee 888°M. Mee eeeeeee eee eeeeeee eeeeeeeeee eeeee e eeeeee ee M8 eeeee eeeeeeeeee. M8M (88 eM) eee eeeee eee eee eeeeeee eee eeeeee eeee e eeeeeeeeee eeeeee eeeeeeeeee MeMMe (88 eM). Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee) eeeeeeee eee eeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.