Science of Synthesis

Hirsch, A.; Vostrowsky, O., Science of Synthesis, (2008) 43, 51.

Currently, the Cadiot–Chodkiewicz reaction (‌Scheme 12‌) is one of the most widely used methods for the coupling of a terminal alkyne ‌41‌ to a 1-bromoalkyne to give a buta-1,3-diyne ‌42‌. The procedure tolerates a wide variety of functional groups and permits the syntheses of numerous functionalized alka-1,3-diynes, but arylated buta-1,3-diynes are generally obtained in higher yields than their aliphatic analogues.[‌143‌]

‌Meeeee 88‌ Meeeee–Meeeeeeeeee Meeeeeeeeeeeee ee Meeeeee eeee 8-Meeeeeeeeeee[‌888‌–‌888‌]

Mee eeeeeeee eeeeeeee eeeeeee eeeee eeeee ee eeeeeeee ee eee eeeeeee eee eeeeeee eeeeeeeeee, eeeeeeeeeeeee eeeeeeeeeeeee, eee eeeeee(M) eeeeeee ee eeeeeeeee. Meeee eeee 8-eeeeeeeeeeee (eeee ee eeeee eeee ee ee eeeeeeee eee eeeeeee eeee-eeeeeeee), eeeeeeeeeee eee eeee eeee ee eee eeeeeeeeeee eeeeeeee eeeeeeee;[‌888‌–‌888‌] 8-eeeeeeeeeeeee eee ee eeeeee eeeeeeeeee eeeeeee ee eeeee eee eeeeeeeeee. Mee eeeeeeeee eee ee eeeeeeeee eeeee e eeeeeee ee eeeeeeeeee, eee eeee eeee eeeeeee ee eeeeee ee eeeee ee eeeeee eee eeeeeeeee ee eee eeeeeee, eee eeeeeeee eeeeeeeeeee, eee eeee, eee eee eeeeee eeeeeeeeee.[‌888‌] Meee-eeeeeeee ee eeeeeeeee eeeeeeee eeeeee eeeeeeeeeeeeeee eeee eeeeeeeeeee eee eeeeeeeeeeee (eeeeeeeee Meeeee–Meeeeeeeeee eeeeeeee); eeee eeeeeeeeeee eeee eeeeeeee ee eeeeeeeeee ee eeeeeee eee eeeeeee–eeeee eeeeeeee.[‌888‌]

M eeeeeeeee ee 8,8-eeeeeeeeeeeeeee eeeeeeeeeee eeee-8,8-eeeeee (M8M≡M—M≡MM8) eeeeeeee eeee eeeeeeeeee (M8M≡MM) eee eeeeeeeeeeeeee (MM≡MM8) eee eeeee ee ‌Meeee 8‌. Meee, e eeeeeeeeeeeeeeeee (eeeee 8), eeeeeeeeee ee e eeee-8,8-eeeee-eeeeee eeeeeeeeeee eee ee eeeeeeeeeeeeeeee, ee eeeeeeee ee eee eeeeeeeeeeeeee ee eee eeeeeeeee “eeeeeeeeeeeeeeeeeeee”.[‌888‌–‌888‌] Me eeeeeeeee eeeee eeeeeee ee eeeee eee ee eeeeeeee ee eee eeeeeeeee-eeeeeeeee eeee (eeeee 8) ee e Meeeee–Meeeeeeeeee eeeeeeee ee eee eeeeeeeeeee eeeeee eeeeeee eeeeeeeee eee ee eeeeeeeeeee eeeee.[‌888‌,‌888‌] M eeee ee eeeeeeeeeeeeee eee eeeeeeeeee ee eeeeeeee ee eee eeeeeee eee eeeee eeeeeee eeeeeeeee. Mee eeeee eeee ee eee eeeeeee eeeeeeeee eee eeeee eeeeeeeeeee ee e Meeeee–Meeeeeeeeee eeeeeeee ee eeeee ee eeeeeeeee eee eeeeeeeee ee eee eeeeeee eeeeeee,[‌888‌] eee eee eeeeeeeee eeeeeeeeee (eeeee 8) ee eee eeeeeeeee eeeeee eeeeeeee eeeeee eee ee eeeeeeeeeee eeee ee eeeeeeeee eeeeee eeeeeeeeeee eeeeeee eeeeeeee eeee M-eeeeeeeee.[‌888‌] Me e eeeeeee eeeeeeeee e Meeeee–Meeeeeeeeee eeeeeeee eeee ee eeeeeeeee eeeeeeeee eeeeeee eeee eeeeee eeeee eee eeeeee M-eeeeeeeee eeeee (eeeee 8), eeeee eeee eeeeeeeeeee eeeeeee eeeeeeeeeee, eeeeeee eeeeeee eeeeeeeeee.[‌888‌] Me eeeeeeeeeee eeeeeeeee ee eeeeeeeeeee eee eeee eee eeee eeeeeeeeeeee eeeeeeeee e Meeeee–Meeeeeeeeee eeeee eeeeeeee (88% eeeee) eeeeeee eeeeeeeeee eee eeeeeee eeeeee ee eee eeeeeeeee (M,M)-8,8-eeeeeeeeeeeeee-8-eee eee (M)-8-eeeee-8-eeeeeeeeeee-8-ee-8-eee.[‌888‌] Me eeeeeeeeeeeeeee eeeeeeeee ee e eeeeee eeeeeeeeee eeeee eeee (eeeee 8) eeeeeee e eeeee eeee eeee eeeeeeee ee e Meeeee–Meeeeeeeeee eeeee eeeeeeee,[‌888‌] eee eee eeeeeeeeee ee eeeeeee ee e eeeeee ee eeeee eeeeeeeeee eeeee eeeee, eeeee ee eeeee eeeeee, eeee eeee eeeeeeee ee eee eeeee ee Meeeee–Meeeeeeeeee eeeeeeeeeeeeeee.[‌888‌–‌888‌] Meeeeeeee eeeeee eeeeeeeeeeeee eeee eee eeeeeeeee eeeee eeeeeeeeeee eee ee eeeeeeeeeee ee eeeeeeeeeeeeee 8-eeeee-8-eeeeeeeeeeee eeee eeeeeeee eeeeeee eee eee-8-eeeeee (e.e., eeeee 8).[‌888‌] Me eeeee eeee, eee eeeeeeee eeeeeeeee 8-eeeeeee-8,8,8-eeeeeeeeeeeeeeeeeeee eeeeeeeee Meeeee–Meeeeeeeeee eeeeeeee eeee 8-eeeeeeeee-8-ee-8-ee ee eeeee eee eeeeeeee eeeeeeeeeeeeeeeeeeeeeee (eeeee 8),[‌888‌] eeeee eee ee eeeee-eeeeeeeee ee eeeeeeeeeeeeee ee ee eee eee(eeeeeeeeee) eeeeeeee eeeeeee eeeeeeeee ee eeee-eeeeeeeeeee eeeeeeeeeeeee. Meeee eeeeeeee ee eeeeeeee eeeeee eeeeeeeeee, eeeeeeeee ee eeeeeeeeee ee eee eeeeeeeeeeeee, eeeeeeeee eeeeeee eee eeeeeeeeeeeee eeeeeeeeeee eeeee ee eeeeeeeeeee eeeeeee (eeeee 8),[‌888‌] eeeee ee e eeeeeeeeeeeee eeee eee Meeee Meeeeeee Meeeeeeee eeeeeee. M Meeeee–Meeeeeeeeee eeeeeeee eee eeee ee eeeeeeee ee eeeee ee eee eee 8-eeeeeeee-8,8-eeeeee eeee ee e eeeeeeeee eeee ee e eee eeee ee eeeeeeeee ee eeeee eeeeeeeeeeeeee eeeeeeeee (eeeee 8).[‌8‌,‌888‌] M eeeeeee eeee ee eeeeeeeeeeeeee ee e eeeeeeeeeee ee eeeeeee eee eee eeeeeeeeeee ee e eeee-8,8,8,8,88,88-eee eeee eee eeee-8,8-eeeee eeeeeeeee (eeeee 88) eeee ee eeee ee e eeeeeeee eeeee eee eee eeeeeeeee ee “eeeeeeee” eeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeeee.[‌888‌] Me eeeeeee eeeeeee, e Meeeee–Meeeeeeeeee eeeee eeeeeeee eeeeeee 8-eeeeeeeeeeeeeeee eeeeeee eee (M)-8-eeeeeeeeeeeee-88-ee-8-eee eeeee ee eee M88-eeeeeeeeeeeeeee eeeeeeeeeeeee M (eeeee 88), e eeeeeeeeee ee eeeeee eeeeeee, ee 88% eeeee.[‌888‌] Meeeeee eeeeeeeee ee eeeeeeeeeeeeee M eee M eeee e Meeeee eeeeeeeeee eeeeeeeee ee ee eeeee ee eee eee eeeeeeeeeeeeeee ee eee eeeeee eeeeee eee Meeeee–Meeeeeeeeee eeeeeeee ee eeee eee eeeee eeeeee.[‌888‌] Meeeeeeeee eeeeeeeeeeeeee eeeee, eeeeeeeee eeeeeeee M eee M, eee eeeeeeeee eeee Meeeeeeeee eeeeeee;[‌888‌] eeeee, e Meeeee–Meeeeeeeeee eeeeeeee ee eeee ee eeeeeeeee eee eeeee eeeeeee ee eeeee eeeeeeeee. Mee eeeeeeeee ee eee eeeeee eeeeeeee ee eeeeeee, e eeeeeeee eeeeeeee eeee eeeeeeeeeeeee, ee eeeeeee eeee eeee eeeeeee eeee e Meeeee–Meeeeeeeeee eeeeeeee (eeeee 88); eee eeeee eeeeeeee ee eeee eee eeee eeee eee eeeeeeeeeeee ee eee eeeeeeee eeeeeeee eee eeeeeeeee.[‌888‌] Mee eeeee eeeeeee ee eeeeeeeeeeeeee (eee eeeee 88), e eeeeeeeee eeeeeeeee eeeeeeeee ee eeeeeeeeeee, eeeeeeeee eeeeee eeee Meeee, ee eeee eeeeee eeeeeee e Meeeee–Meeeeeeeeee eeeeeeee,[‌888‌] eee eee eeeeeeeee ee ee eeeeeeeeeeee eeeeeeeeeee eeee eeeee (eeeee 88) eeeeeeeee eeeeeee e Meeeee–Meeeeeeeeee eeeeeeee eeeeeeee ee eeeee ee eee eeeee eeeeeee.[‌888‌] Meeeeeee, e eeeeee ee eeeeeeeeeeeee eeeeee (e.e., eeeeeee 88 eee 88) eee eeeeeeee ee eee Meeeeeeeeee eeeeeeeeeeeeee ee eeeeeee- eee eeeeeee-eeeeeeeeeee eeeeeeeeee eee eeeeeeeeeeeeee. Meeeee eeeeee 88%, eee eeeee eeeeeeee eee eeeeeeeeeeee eeeeeeeee eeee eee eeeeee eeeeeeeeeeeeee eeeee ee eeeeeeeeeeee.[‌888‌]

‌Meeee 8‌ 8,8-Meeeeeeeeeeeeee Meeeeeeeeee Meee-8,8-eeeeee ee eee Meeeee–Meeeeeeeeee Meeeeeeeeeeeee ee Meeeeeee Meeeeeeeee eee Meeeeeeeeeeeee[‌8‌,‌888‌–‌888‌,‌888‌,‌888‌,‌888‌,‌888‌–‌888‌,‌888‌,‌888‌,‌888‌–‌888‌]

Meeee	M8	M8	M	Meeeeeeeee	Meeee (%)	Mee
8			Me	MeMe, MeMM8, MM8MM•MMe, MeMM	88	[‌888‌–‌888‌]
8			M	MeMe, MeMM8, MM8MM•M8M, MeMM	88	[‌888‌]
8			Me	MeMe, MeMM8, MM8MM•MMe, MeMM, eeeeeee, 8°M	88	[‌888‌]
8			Me	MeMe, MeMM8, MM8MM•MMe, MeMM, 8°M	88	[‌888‌]
8		(MM8)8Me	Me	MeM, MeMe8(MMe8)8, MeMM8, eeeeeee, ee	88	[‌888‌]
8	MM=MMMM8Me		Me	MeMe, MM8MM•MMe, MeMM8, MeMM, 8°M	88	[‌888‌]
8		MM8MM	Me	MeMe, MeMM8, MeMM	88	[‌888‌]
8			Me	MeMe, MeMM8, MM8MM•MMe, M8M, MeMM, 8°M	88	[‌888‌]
8			Me	MeMe, eee MMM, MeM, MeMM8, −88 ee 88°M	88	[‌8‌]
88		MMe8M≡MMMMM	Me	MeMe, eee MMM, M8, MeMe, eeeeeeee, 8°M	88e	[‌888‌]
88		MM8MM	Me	MeMe, MeMM8, MM8MM•MMe, MeMM, M8M	88	[‌888‌]
88		(M)-MM=MMMM8MM	Me	MeMe, MM8MM•M8M, MMM, MMM, 8°M ee ee	88	[‌888‌]
88		(M)-MM=MMMM8MM	Me	MeMe, MeMM8, MM8MM•MMe, MeMM, M8M, 8°M	88	[‌888‌]
88		Me	M	MeM, eeeeeeeeeee, ee	88	[‌888‌]
88	MeMe8(MM8)8MM		M	MeM, eeeeeeee eeeeeeeeee, ee, 8 e	88	[‌888‌]
88			M	MeM, eeeeeeee eeeeeeeeee, ee, 8 e	88	[‌888‌]

e Meee eeeeee eeeeee ee M8M≡MM eeeee eeee 8 eeeeeeeeeee ee M8M≡MM.

Me eeee eeeee eeeeeeeeeeeee 8,8-eeeeeeeeeee eeee-8,8-eeeeee eee ee eeeeeeee ee Meeeee–Meeeeeeeeee eeeeeeeee. Meee, eeee eeee-8-eeeee eeee (‌88‌) ee eeeeeee eeee 8-eeeeeeeee-8-eeeee eeee (‌88‌), eeee-8,8-eeeeeeeeee eeee (‌88‌) ee eeeeeeee ee 88% eeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meee-8,8-eeeeeeeeee Meee eeee e Meeeee–Meeeeeeeeee Meeeeeee Meeeeeee[‌888‌]

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) M 8-8, 888.
• 8.Meeeee-Meee, (8888) M 88-8, 8888.