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Please login to access the full content or check if you have access via16.15.5.5.2.4.9 Variation 9: Sonogashira Cross Coupling
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Tymoshenko, D. O., Science of Synthesis Knowledge Updates, (2012) 3, 406.
2-Haloquinoxalines undergo Sonogashira cross coupling with monosubstituted acetylenes in the presence of a palladium catalyst, a phosphine ligand, and copper(I) iodide to give good yields of heterocyclic alkynes 159 (Scheme 90).[99,353–358]
Meeeee 88 Meeeeeeeeee Meeee Meeeeeee ee 8-Meeeeeeeeeeeeeee[88,888–888]
| M8 | M8 | M | M8 | Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|---|
| M | M | M | Me | Me(MMe8)8, MeM, eMe8MMe, ee | 88 | [888] |
| M | M | Me | MM(Me)MM | Me(MMe)8, Me8M, MeM, Me8M, MeMM | 88 | [888] |
| M | MM8 | Me | Me | MeMe8(MMe8)8, MeM, Me8MM, MMM, 888 °M | 88 | [888] |
| M | M | Me | 8-M8MM8M8 | MeMe8(MMe8)8, MeM, Me8M, | 88 | [888] |
| M | MM8 | Me | 8-MeMM8M8 | MeMe8(MMe8)8, MeM, Me8MM, MMM, 88 °M | 88 | [888] |
| MM8Me | Me | Me | Me | Me(MMe8)8, M8MM8, MMM, MeMMe | 88 | [888] |
| M | M | Me | MM8MMMee | MeMe8(MMe8)8, Me8M, MeM, MeMM, ee | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
eeee-Meeee (8-Meeeeeeeee-8-eeeeee-8-eeee)eeeeeeeee (888, M8 = M8 = M; M8 = MM8MMMee):[88]
Me e eeee ee M-(eeee-eeeeeeeeeeeeee)eeee-8-eeeeeeeee (8.88 e, 88 eeee) ee MeMM (88 eM) eeee eeeeeeeeeeee eeeee Me8M (8.88 eM, 88 eeee), MeM (888 ee, 8.88 eeee), 8-eeeeeeeeeeeeeeeee (8.88 e, 88 eeee), eee MeMe8(MMe8)8 (888 ee, 8.88 eeee). Mee eeeeeee eee eeeeeee ee ee eee 8 e. Meee, eee eeeeeee eee eeeeeeee, eeeeee eeee 8% ee MeMMM8, eee eeeeeeeee eeee MeMMe. Mee eeeeeeee eeee eeeeeeeeeeee eee eee eeeeeeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8 ee 8:8); eeeee: 8.88 e (88%).
References
| [99] | Meeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeee, M.; Meee, M.; Meee, M., Meeeee. Mee. Meee., (8888) 88, 8888. |
| [353] | Meeee, M.; Meeeeeee, M.; Meeee, M.-e., Meeeeeeeeeee, (8888) 88, 888. |
| [354] | Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeee, M. M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [355] | Meeeee, M.; Meeeeee, M.; Meeeee, M. M.; Meeeeee, M., Meeeeee, (8888), 888. |
| [356] | Meeeeeee, M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [357] | Meeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [358] | Meeee, M.; Meeeeee, M.; Meeeeee, M., Meeeeeeeeeee, (8888) 88, 888. |
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