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3.4.2.6 Method 6: Copper/Palladium-Catalyzed Coupling Reactions of Terminal Alkynes with Organic Halides

DOI: 10.1055/sos-SD-003-00274

Heaney, H.; Christie, S.Science of Synthesis, (20043402.

The fact that the reactions discussed in Sections 3.4.2.1 and 3.4.2.2 require stoichiometric alkynylcopper(I) derivatives has on occasions presented major problems because of the instability of the reagents. In addition, the vigorous reaction conditions that are sometimes required limit the types of functional groups that can be tolerated. The discovery that the coupling of terminal alkynes with iodoarenes, bromopyridines, and alkenyl bromides could be carried out rapidly, frequently at room temperature, in the presence of catalyst systems comprising dichlorobis(triphenylphosphine)palladium(II) and copper(I) iodide in triethylamine, without the isolation of the copper(I) derivative, provided a major advance. It was also established that tetrakis(triphenylphosphine)palladium(0) can be used together with copper(I) iodide in diethylamine.[‌620‌] Similar coupling reactions using palladium catalysis in the absence of copper(I) salts were reported at about the same time, but those reactions require much more forcing reaction conditions.[‌621‌‌623‌] It is interesting to note that Heck reactions have been carried out without the use of stabilizing ligands by using palladium deposited on porous glass,[‌624‌] and it is also possible that polymeric phosphine-terminated ligands[‌625‌] could prove to be valuable in conjunction with copper(I) salts in alkyne coupling reactions. The catalyst system tris(dibenzylideneacetone)dipalladium together with tri-tert-butylphosphine has also been identified for room temperature coupling of aryl bromides in the absence of copper(I) iodide.[‌626‌]

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8-eeeeeeeee-8-ee-8-ee 8-eeeeeeeeeee 8-(8,8-eeeeeeee-8-eeeeeeeeee-8-eeee)eeeeeee 88 88°M 88 [‌888‌]
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8-eeeeeeeeee-8-ee-8-ee 8-eeeeeeeeeeeee 8-eeeeee-8-(8-eeeeeee)eeee-8-ee-8-ee 88 88°M 88 [‌888‌]
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8-eeeeeeeee-8-ee-8-ee 8-eeeeeeeeeeee 8-(8-eeeeeeeeeeeee)-8-eeeeeeeee-8-ee-8-ee 88 ee 88 [‌888‌]
8-eeeeeeeee-8-ee-8-ee 8-eeeeeeeeeeeeeeeee 8-(8-eeeeeeeeeeee)-8-eeeeeeeee-8-ee-8-ee 88 ee 88 [‌888‌]
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8-eeeeeeeeeeeeeeeeeee 8-eeeeeeeeeeeeeeeee 8,8-eeeeee-8,8-eeeeeeeeeeeeeeeeee 88 ee 88 [‌888‌]
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8-eeeeeeeee-8-ee-8-ee eeeeee 8-eeeeeeeeeeeee eeeeee [8-(8-eeeeeee-8-eeeeeeeee-8-eeee)eeeeeeee 88 88°M 88 [‌888‌]
M-eeeee-M-eeee-8-eeeeeeeeeeeee eeeeeeeeeee M-eeeee-M-(8-eeeeeeeeee-8-eeee)eeeeeeeee 88 ee 88 [‌888‌]
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eeeeeee(eeeeeeeee)eeeeee 8-eeee-8-eeeeeeeeeeee 8-eeeeee-8-[(eeeeeeeeeeeeee)eeeeeee]eeeeee 88 88°M 88 [‌888‌]
eeeeeee(eeeeeeeee)eeeeee 8-eeeeeee-8-eeeeeeeeee 8-eeeeeee-8-[(eeeeeeeeeeeeee)eeeeeee]eeeeee 88 88°M 88 [‌888‌]
eeeeeee(eeeeeeeee)eeeeee 8-eeeee-8-eeeeeeeeeee eeeeeee 8-eeeee-8-[(eeeeeeeeeeeeee)eeeeeee]eeeeee eeeeeee 88 88°M 88 [‌888‌]
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eeeeeee(eeeeeeeee)eeeeee 8-eeeeee-8,8-eeeeeeeeeeeeeeee 8,8-eeeeeeee-8-[(eeeeeeeeeeeeee)eeeeeee]eeeeeeee 8 888°M 88 [‌888‌]
eeeeeee(eeeeeeeee)eeeeee (eeeeee) 8,8,8-eeeeeeeeeeeeeee 8,8,8-eeee[(eeeeeeeeeeeeee)eeeeeee]eeeeeee 8 88°M 88 [‌888‌]
eeeeeee(eeeeeeeee)eeeeee 8-eeee-8,8-eeeeeeee-8M-eeeeeee-8-eeeeeeeeeeee 8,8-eeeeeeee-8-[(eeeeeeeeeeeeee)eeeeeee]-8M-eeeeeee-8-eeeeeeeeeeee 8 88°M 88 [‌888‌]
M,M-eeeeeeeeeeee-8-ee-8-eeeee 8-eeeeeeeeeeeeeee M,M-eeeeeeee-8-(eeeeeeeee-8-ee)eeee-8-ee-8-eeeee 88 88°M 88 [‌888‌]
8-eeeeeeeeee-8-ee-8-ee 8-eeeeeeeeeeeee 8-eeeeee-8-(8-eeeeeee)eeee-8-ee-8-ee 88 88°M 88 [‌888‌]
(e) eeeeeee(eeeeeeeee)eeeeee; (e) eeeeeee(eeeeeeeeeeee)eeeeee 8-eeeee-8-eeeeeeeeeee 8-[(eeeeeeeeeeee)eeeeeee]-8-[(eeeeeeeeeeeeee)eeeeeee]eeeeeee 8 ee 88 [‌888‌]
eeeeeee(eeeeeeeeeeee)eeeeee M,M-eeeeeee-8-eeeeeeeeeee M,M-eeeeeee-8-[(eeeeeeeeeeeeeeeee)eeeeeee]eeeeeee 8 ee 88 [‌888‌]
eeee-8,8-eeeeee(eeeeeeeee)eeeeee M,M-eeeeeee-8-eeee-8-[(eeeeeeeeeeeeeeeee)eeeeeee]eeeeeee M,M-eeeeeee-8-[(eeeeeeeeeeeeeeeee)eeeeeee]-8-[(eeeeeeeeeeeeee)eeee-8,8-eeeeee]eeeeeee 8 ee 88 [‌888‌]
eeeeeeeeeeeeeee 8-eeeeeeeeee eeeeeee 8-(eeeeeeeeeeeee)eeeeee eeeeeee 88 88°M 88 [‌888‌]
eeeeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeeeee 88 eeeeeeeee 88 [‌888‌]
eeeeeeeeeeeeeee 8-eeeeeeeeeeeeeeee 8-(8-eeeeeeeeee)eeeeeeee 88 eeeeeeeee 88 [‌888‌]
eeeeeeeeeeeeeee 8-eeeeeeeeeeeee 8-(eeeeeeeeeeeee)eeeeeeeee 88 eeeeeeeee 88 [‌888‌]
eeeee-8-eee 8-eeeeeeeeeee 8-(eeeee-8-eeee)eeeeeee 88 eeeeeeeee 88 [‌888‌]
eeeeeee(eeeeeeeee)eeeeee 8-eeeee-8-eeeeeeeeeee 8-eeeee-8-(8-eeeeeeeeeeeeeeeeeeeee)eeeeeee 88 ee 88 [‌888‌]
eeeeeeeeeeeeeee 8-eeeeeeeeeee 8-eeeeeee-8-(eeeeeeeeeeeee)eeeeeee 88 ee 88 [‌888‌]
eee-8-eee eeeeeeeeeee eee-8-eeeeeeeeeee 88 ee 88 [‌888‌]
eeeeeeeeeeeeeee 8-eeeeeeeeeee 8-eeeeeee-8-(eeeeeeeeeeeee)eeeeeee 88 ee 88 [‌888‌]
eee-8-ee-8-ee 8-eeeeeeeeeee 8-(8-eeeeeeeeeeeee)-eee-8-ee-8-ee 88 ee 88 [‌888‌]
8-eeeeeee-8-eeeeeeeeeeeeee eeeeee 8-eeeeeeeeeeee eeeeee 8-[(8-eeeeeeeeeeeee)eeeeeee]eeeeeeee 88 88°M 888 [‌888‌]
8-eeeeeee-8-eeeeeeeeeeeeee 8-(8-eeeeeeeeee)eeeeeeee 8-{8-[(8-eeeeeeeeeeeee)eeeeeee]eeeeee}eeeeeeee 88 88°M 88 [‌888‌]
8-eeeeeee-8-eeeeeeeeeeeeee 8-eeee-8-eeeeeeeeeeee 8-eeeeeee-8-[(8-eeeeeeeeeee)eeeeeee]eeeeeee 88 88°M 88 [‌888‌]
8-eeeeeee-8-eeeeeeeeeeeee 8-(8-eeeeeeeeee)eeeeeeee 8-{8-[(8-eeeee)eeeeeee]eeeeee}eeeeeeee 88 88°M 88 [‌888‌]
eeeeeee(eeeeeeeee)eeeeee 8-eeeeeeeeeeeee 8-eeeeeee-8-(eeeeeeeeeeeeee)eeeeeeee 88 ee 88 [‌888‌]
eeeeeee(eeeeeeeee)eeeeee 8-eeeee-8,8-eeeeeeeee 8-eeeeeee-8-(eeeeeeeeeeeeee)-8,8-eeeeeeeee 88 ee 88 [‌888‌]
eeeeeee(eeeeeeeee)eeeeee 8,8-eeeeeee-8,8-eeeeeeeee 8,8-eee(eeeeeeeeeeeeeeeeeeeee)-8,8-eeeeeeeee 88 ee 88 [‌888‌]

e Meeeeeee: (8) MeMe8(MMe8)8, MeM, Me8MM; (8) MeMe8(MMe8)8, MeM, Me8M; (8) MeMe8(MMe8)8, MeM, Me8MM, MMMM; (8) Me(MMe8)8, MeM, Me8M, eeeeeee; (8) MeMe8, Me8M, MeM, Me8M; (8) MeMe8, Me8M, MeM, Me8M, MeMM; (8) Me8M, 88% Me/M, MeM, Me8M, MeMM; (8) Me(MMe)8, Me8M, MeM, Me8M; (8) Me(MMe8)8, MeM, Me8MM; (88) MeMe8(MMe8)8, MeM, eeeeeeeeee; (88) Me8M, 88% Me/M, MeM, M8MM8, M8M/MMM; (88) MeMe8(MMe8)8, MeM, M8MM8, Me8M, M8M; (88) Me(MMe8)8, MeM, MeMe8MMe, eeeeeee, 8.8M MeMM; (88) MeMe8(MMe8)8, MeM, Me8M, MMM; (88) e-Me8M, MeMe8(MMMe)8, MeM, eMe8MM; (88) Me(MMe8)8, MeM, Me8MM, MMM; (88) Me(eee)8, Me8M, MeM, eMe8MMe; (88) Me(MMe8)8, MeM, Me8M/eeeeeeee; (88) Me(MMe8)8, MeM, Me8M, MMM; (88) Me(MMe8)8, MeM, Me8M, MMM; (88) MeMe8(MMe8)8, Me8M, MeM, Me8M; (88) MeMe8(MMe8)8, Me8M, MeM, Me8M/eeeeeeee; (88) Me(MMe)8(MMe8)8, MeM, Me8M, MMM; (88) MeMe8(MMe8)8, MeM, Me8M, eeeeeee; (88) MeMe8(MMe8)8, MeM, Me8MM, MMM; (88) Me8M, 88% Me/M, MeM, M8MM8, M8M, MMM; (88) Me(MMe8)8, MeM, Me8M; (88) Me, Me8M, MeM, MM, Me8M8; (88) MeMe8(MMe8)8, Me8M, MeM, eeeeeeeeee; (88) MeMe8(MMe8)8, MeM, MMMM, MMM; (88) MeMe8(MMe8)8, MeM, MMMMM, MMM; (88) Me8(eee)8, (8,8,8-Me8M8M8)8M, MeM, eMe8MMe, MMM; (88) MeMe8(MMe8)8, MeM, eMe8MM; (88) MeMe8(MMe8)8, MeM, eMe8MM, MMM.

Me ee eeeee eeeeeeeeeeeee, ee eee eeee eeeee eeee eeeeeeeee eeee eeee eeeeeeeee eeee eeee eeeeee ee eeeeeee eee eeeeeeeee eeeeeeeee eeee eeeeee.[‌888‌] Meee, eeeeeeeeeeeeeee eee eeeee ee eeee eeee-eeeee eeeeeeeeeeeee eeeeee ee 88% eeeee ee e eeeeeeee eeee eeeeeeee eeeeeeee eee 8-eeeee eeeeeeeeeeeee eeeeee ee 88% eeeee ee e eeeeeeee eeee 8-eeeeee eeeeeeee. Meee eeeeeeeeee eeeeeeee eee eeeee ee Meeeee 888. Meee eeeeeee eeeeeee eeee eeee eeee eeeeeeee, eee eeeeeee 8-eeeeeeeeeeeee eeeeeeeeeeeee eeeeee eee eeeeeeee ee 88% eeeee ee eee eeeee-eeeeeeeee eeeeeeee ee 8-eeee-8-eeeeeeeeeeeeee eeee eeeeee eeeeeeee eee eeeeeeeeeeeeeee ee eeeeeee eeeeeee ee eeee eeeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee (8eee%) eee eeeeee(M) eeeeee (8eee%).[‌888‌]

Meeeee 888 Meeeeeeee ee Meee Meeeeeeee eee M,M-Meeeeeeeeeeeeeeee Meeeeeee eeee Meeeeee ee eee Meeeeeeee ee Meeeeee eee Meeeee[‌888‌]

Me ee eeeeeee eeee eeeee eeeeeee ee eee eeeeeeee eeeeeee MeeeeeeeeeeMeeeeeee eeeeeeee eeeeeeeee ee e eeeeee ee eee eeee eeee eeeee eeeeee eeeeeeeee ee β-eeeeeeeeeee eeeeeeee eeee eee eeeeeeee eeeeeee. Me eeeeeeeee ee eeee eeeeeeeeeeeeee ee eeee ee eeeeeeeeee eeeeeeeeee, ee eeeee eeeee ee e eeee eeeeeeeeee ee e-eeeeeeeee ee eee eeeeeeeee eeee, eeee eeeeeee eeeeeeee eeeee eeeeeee eeeeeeee eeeeeeeeee. Meeeeee, eee eeeeeeee, ee eeeeeeeeeee ee Meeeee 888, eeee eee eeeeeeee eee eeeeeee-eeeeeeeeeee eeeeeeeeeeeeeeeee eeeeeeeeeee, eeeeeeeeee eeeeee ee eeeeeeeeeeeee ee eee eeeeeeeee eeeeee eeeeeeeeeeeee eeeeeeeeeee eee eee eeeeeee eeeeeeeeeeeeeeeee eeeeeeeee.[‌888‌]

Meeeee 888 Meeeeeeee ee Meeeeeeeeee eeee Meeeeeee Meeeeee ee eee Meeeeeee ee Meeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8) eee Meeeee(M) Meeeeee[‌888‌]

M eeeeeeee eeeeeeeeeee eeeeeeee eee eee eeeeeeee eeeeeeeee eee ee eeeeeee eeee eee eeeee eeeeee ee eeeeeeeeeee eeee ee eeeeeeeee. Mee eeeeeeeee eeeeeeee ee eee eeeeeee ee eeee eeeeee ee e eeeeeeeee(8) eeeeeee eee eee eeeeeeeeeee eeee ee eeeeeeeeeeeee(M) eeeeeeeeeeee, eeeeeeeee eeee eee eeeeee eee eee eeeee ee eee eeeeeeee ee eee eeeeee(M) eeee, eee eeeeeee ee ee eee eee eeeee ee eee eeeeeee. Meeee eeeeeee ee 8,8-eeeeeeeeeeeee eeee-8,8-eeeeee eee eeeeee ee eeeeeeeeee eeee eeeee e eeeeeeeee(MM) eeeeeee. Mee eeeeeeeeeeeeeeeeee eeeeeee ee eeeeeeeeeeeeeeeeeee(M) eee eeee eeeee ee eeeee eeee eee eeeee-eee(eeeeeeeeeeeeeeeee)(eeee)(8-eeeee)eeeeeeeee eeeeeee ee eeee eee eeeee-eeeeeee eeeeeee ee 88% eeeee,[‌888‌] eee eeeeee eeeeeeee eee eeee eeee eeeeeeeeeeee.[‌888‌] Meeeee(M) eeeee eee eeeee ee eeeeeeeeee eee eeeeeeeeeeee ee eeeeeee.[‌888‌] Me eeeeeeee, ee ee eeeee eeee e eeeee-σ-eeeeeee eeeeeee ee eeeeee eeee eeeeee ee eee eeeeeeee ee eeeeeeeeeee(eeeeeeeeeeeeeeeee)eeeeeeeee eeee eeeeeeeeeeeeeee ee eee eeeeeeee ee ee eeeeeeeee eeeeee ee eeeeeeeeeeee eee e eeeeeeeee eeeeee ee eeeeee(M) eeeeee, eee eeee eeee ee eeeeeee eee eeee eeee ee eee eeeeeee eeeeeee ee e eeeeeeeee eeeeeeeeeee eeeeeee.[‌888‌] Mee eeeeee ee eee eeeeeee eeeeeee ee eeeeeeee eeeeeee ee eee eeeeee ee eeeeeeeee(MM) eeeeeee eeee, eeeeeeeeee ee eee eeeeeeeee eeeeeeeeeee ee eee eeeee eeee e eee(eeeeeee)(eeeeeeeee)eeeeeeeee eeeeeee.[‌888‌] Mee eeeee-eee(eeeeeeeeeeeeeeeee)eeeeeeeee eeeeee eeeeeee eee eee eeeee-eee(eeeeeeeeeeeeeeeee)eeeeeeeee eee(eeeeee eeeeeeeeee) eeeeeee eeee eeee eeeee ee eeeeeee eeeeeeeeeeeeeeeeee ee eeee eeeeeeeeeee ee eee eeeeeeee ee eeeeee(M) eeeeee ee 88% eeeee, eee ee eee eeeeeee ee eeeeee eeeeee eee eeeee ee eee eeeee-eee(eeeeeeeeeeeeeeeee)(eeee)(eeeeee eeeeeeeeee)eeeeeeeee eeeeeee eee eeee 8% eeeee e eeeeeeeee eeeeeeee eeee.[‌888‌]

Me eee eeee eeeee eeee 8,8-eeeeeeeeeeeee eeeeeeeeeee ee eeee-8,8-eeeee eee ee eeeeeeee ee eeee ee eeeeeeeee eeeeee eeee eeeeeeee eeeeeee eee eeeeeee ee eeeee ee eeeeeee eeee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee eee eeeeee(M) eeeeee ee eee eeeeeeee ee 8 eeeeeeeeeee ee eeeeeeeeeeeee eee eee eeeeeeeeee ee eeeeeeeeeeeee.[‌888‌] Mee eeeeee eee eeee eeee eeee ee eee eeeeeeeeeee ee 8,8-eeeeeeeeeeeeee-8,8-eeeee eeeeeeeeeee ee eee eee ee eeeeeee eeeeeeeeeee eeeeeeeeeeeee.[‌888‌,‌888‌] Meee ee eee eeeee ee eeeee ee Meeeee 888.[‌888‌]

Meeeee 888 Meeeeeeeeeeee-Meeeeeee Meeeeeeeeeee ee eee Meeeeeee ee Meeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8) eee Meeeee(M) Meeeee[‌888‌]

M eeeeeeee eeeeeeee eee eee eeeeeeeeeee ee e eeee eeeee ee eeee 8,8-eeeeeeeeeee-8,8-eeeee eeeeeeeeeee eee 8,8-eeeeeeeeeeee-8,8-eeeee (88) eeee eeeeeeee eeeeeee, ee eeeeee eeeeeee eeee 88 ee 88%, eeeeeeee eee eee ee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee, eeeeee(M) eeeeee, eeeeee, eee eeeeeeeeeeeeeeee (Meeeee 888).[‌888‌] Meeeee eee eeeeeeeeeeeee eeeee ee eee eeeeeee ee eeeeee eee ee ee eeeeeee eeee eee eeeeee eeeeeeeee ee eeeeeeeeee e eeeeeeeee(MM) eeeeeee eeee eee eeeeeeeee(8) eeeeeee eeeeeeee ee eee eeeeeeee eeeeeeeee eeeee, eeeee ee eeee ee eee eeeeeeeee ee Meeeee 888. Meeeeeee eee eeeeeee eeee ee eee eeeeee eeeeeeee ee eeeeeee, e eeeeeeeeee eeeeeeeeeee eeeeeeee eeeee eeeeeee ee eee eee eeeeeeeee eeee eee eee eeeeeeeee/eeeeee-eeeeeeeee eeeeeeee eeeeeeeee ee eeeeeee eeee eeeeeee eeeeeee, eee eeee eee eeeeeeeeeeee ee eeeeeee, ee eeeeeeeeee ee Meeeee 888.

Meeeee 888 Meeeeeeee ee 8,8-Meeeeeeeeeee-8,8-eeeee[‌888‌]

Meeeee 888 Meeeeeeeeee Meeeeeee eee eee Meeeeeee ee Meeeeeeeeeeeeee eeee Meeeeeeeeee ee eee Meeeeeee ee Meeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) eee Meeeee(M) Meeeee

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeeeeee-8,8-eeeee (88); Meeeeee Meeeeeeee:[‌888‌]

MeMMM (8.88e, 8.88eeee), MeMe8(MMe8)8 (8.88e, 8.88eeee, 8.8eee%), MeM (8.88e, 8.88eeee, 8eee%), eee M8 (8.88e, 8.8 eeeee) eeee eeeee ee eMe8MM (8eM) eee eee eeeeeee eee eeeeeee ee ee eee 8e. Mee eeeeeee eee eeeee ee e eeeeee (eeeeee eee, eeeeeee). Meeeeee ee eee eeeeeee eeee 88 ee eeeee eeeeeeee; eeeee: 8.88e (88%); ee 8888°M (eee.[‌888‌] ee 8888°M).

References


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