Science of Synthesis

Griesbeck, A. G.; Soldevilla, A., Science of Synthesis, (2008) 43, 365.

In conventional Sonogashira reactions using a copper(I) catalyst, symmetrical diyne byproducts are formed via Glaser-type oxidative couplings, complicating the reaction and reducing the yield. Synthetic strategies for direct palladium-catalyzed coupling have been developed to address this problem. These are a convenient and direct route to arylalkynes, and are carried out without the use of a copper cocatalyst.

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Meeeeee eeeee ee eeeeeeeeee eeee eeeeeeeeeeeeeeeeee eeeee. Meeeeeeeeeeeee eeee eeee eee eeeeeeeeee eeeeee(M) eee ee eeeeeeeeeee ee eeeeee(M), eee eeeeeee eeeeeeeeee eeee ee eeeeeeeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeeeee eeee eeee eeeeeeee eeeeeee:[‌88‌] eee eeeee-eeeeeeee eeeeeeee ee eeeeeee eee ee eeeeeeeee eeeeeeeeeeeeeee, eeeee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8) ee eee eeeeeeee, eeeeee 88–88% eeeeee ee eeeeeee eeeeeeeeeee eeee eeee eeeeeeeeee eee eeeeeeeee eeeeeeee. Mee eeeeeeee eee eeee eeee eeeeeeeee eeee eeeeeeeeeeeeeeeeee eeeeeee ee eee eeeeeeeee eee eeeeeeeee(MM) eeeeeee ee eeee(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeee(8) ee eee eeeeeeee:[‌88‌] eeeee eeeee eeeeeeeeee eeeeeeee eeeeee eee eeeeeeeeee eee eeeeeeeeeee ee eeee eeeeeeeeeee, eee e eeeee eeeee ee eeeeeeeeee eeeeee ee eeeeeeeee.

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M eeeeeeee eeeeeeeeee e eeeee eee eeeeee eeeee eeeeeeee eee eeeeeeeeee ee eeeeeeeee eeeeeeeeeee, eeeeeeeee e eeeeee eeeeeeee eeeeeee, eee eeee eeeeeeee (‌Meeeee 88‌). Meeeeeee eee eeeeeeeee eeeee ee eeeeeeeeeee ee eee ee eeee ee eeee ee eeeeeeee eeeeeeee,[‌88‌,‌88‌] eeeeeeeeeee eeee eeee eee eeeeeeeee eeeeeeeeee eeee eeeeee ee eeeeeeeee eeeeee eee eeeeee.[‌88‌] Mee eeeeeeee ee eeeeeeeee ee e eeeee eeeeee ee eeeeeeeeee, eeeee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) ee eeeeeeee: eeeee eeeeeeee eeeee (88−88 eeeeeee) ee 88°M eeeeee 88–88% eeeeeee eeeeeeeeeee ‌88‌. Me eeeeeeeee eeeeeeee, eeeee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) eeeeeeee eeeeeeeeee eeeee ee e eeeeee eeeeeee, eee eeee eeee eeeeeeeee.[‌88‌]

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Meeeeee eeeeeeeeeee eeeeeee eeeeeee ee eeeeeeeeeeee (‌Meeeee 88‌).[‌88‌] Mee eeeeee eeeeeeee eeeeeeee eeeeee eeeeeeeeeeee (888–888°M), eee eee eeeeeeeeee eee eeeeee eee eeee eeeeeeeeeeee eee eeeeee eeeeeeeee, ee ee eee ee e eeeeee eeeeee eee eee eeeeeeeeeee ee eeeeee eeeeeeeeeee ‌88‌. Mee eeeeee eeeeeeee e eeeeeeeee eeeeeeee eeeeeeeeee eeeeeeeeee eeeee eeeeeeeee eeeeeee (e.e., eeeeeeeeeeeeeeeeeeeeee), eee eeeeee eeeeeeeee ee eee eeee, eee eeeeeee eeeeeeeeeee ee eeee ee eeeeeeeee eeeeee.

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Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeeeeeee (‌88‌, Me8 = M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee MeMe (88.8 ee, 8.88 eeee), eeeeeeeeeeeeeee (88.8 ee, 8.8 eeee), Me8MM8 (888.8 ee, 8.8 eeee), [MeMe8(MMe8)8] (88.8 ee, 8.88 eeee), eee MMMM (8.8 eM) eeeee M8 ee e eeeeee eeee eee eeeeee eeee eeeeeeee ee 888°M eee 88 e. Mee eeeeeee eee eeeeeee ee eeee, eee eeeeeee eeee MM8Me8 ee 8.8 eM. Meeeeeeeee (eeeeeeee eeeeeeee eee MM eeeeeeee; 88 ee, 8.88 eeee) eee eeeee eee, eeeee MM eee MM/MM eeeeeeee, eee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeee MMM (eeeeee eee, eeeeeeeeeee) ee eeee eee eeeeeee ee e eeeeeeeee eeeee; eeeee: 88.8 ee (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.