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Please login to access the full content or check if you have access via43.6.1.3.4 Method 4: Copper/Palladium-Catalyzed Cross Coupling of Haloarenes and Terminal Alkynes (The Sonogashira–Hagihara Cross-Coupling Reaction)
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Griesbeck, A. G.; Soldevilla, A., Science of Synthesis, (2008) 43, 359.
This reaction[60–62] was first reported[63] by Sonogashira and Hagihara in 1975. It can be considered as an application of palladium catalysis (in the sense of the Heck reaction) to the Stephens–Castro reaction. Typically, two catalysts are needed for this process: a palladium(0) complex and a copper(I) halide salt. Phosphine–palladium complexes such as tetrakis(triphenylphosphine)palladium(0) are used for this process; palladium(II) complexes can also be used, as they are reduced to palladium(0) species by the consumption of terminal alkynes in the reaction medium. In contrast, copper(I) halides react with the terminal alkyne and produce copper(I) acetylide, which acts as an activated species for the coupling reactions.
Meeeeeeeeeeeeee, eeeee eeeeeeeee eeeeeeeee eeeeee, M, M, eee M′, eee ee eeeeeeeeeeeee (Meeeee 88).[88] Meeee M eeeeeeeeeee ee e eeeeeeeee-eeeeeeeee eeeee-eeeeeeee eeeeeeee eeeeeee ee ee8-M eeeeee 88 eee e eeeeeeee eeeeee 88, eeeee eeeeeee eee eeeeeeeee eeeeeeee ee eee eeeeeee eeeeee ee e eeeeeeeee(8) eeeeeee eeeeeeee ee eee eeeeeeeee eeeeeeeeeee ee eee eeeeeee 88. Meeeee M eee M′ eeeeeeeeee ee eee eeeeee-eeeeeeeee eeeeeeeeeeee ee eee eeeeeeeee eeeeeeeee (eeeeeeeeeeeeeee), Meeee M′ eeeeee ee e “eeee” eee eeeee M, eeeeeeee ee eeeeeee eeeeeeeee(MM) eeeeeee ee eee eeeeee eeeeeeeee(8) eeeeeee. Me eeee eeee, e eeeeeeeeeeee eeeeeee, 8,8-eeeee 88, ee eeeeee ee e eeeeeeeee. Meeeeeee, 8 eeeeeeeeee ee eeee ee eeeeeeee, ee eeeee ee eeeeeeeeeee eee eeeeeeee eeeeee 88 eee eeee eee eeeeeeeeeeee eeeeee(M) eeeeeeeee. Meeeeeeeeee, eeee ee eeeeeeeeeeeee eee eeeeeeeeeeee, eee eeee eee eeee eeeeeee, eeeeeeeeee ee eeeeeeee: eee eeeeeeee eee, eeeeeee, ee eeeeeeeee ee e eeeeee eee eeeeeeee eee eeeee eeeeeeeeeeeeeee ee eeeeeee, eeee eeee e eeeeee eeeeee ee eee eeeee, eee ee eeeeeee eeeeee ee eee eeeeeeeeeee ee eee eeeeeeee eeeeeee eee eee eeee ee eeeeeeee ee eee eeeeeeeee, eee ee eeee ee eeee ee eeee, ee eee eeeeee, eeeee eeeee eeeeeeeeee eeee eeeee eeeee ee eee eeeeeeeeeee eeeeee.[88]
Meeeee 88 Meeeeeeee ee eee Meeeeeeeeee Meeeeeee[88]
Meeeeeeeeee eeeeeeeee eeee eeee eeeeeeeeeee eeeeee ee eeeeeeeeee ee eeeeeeeeee: eeeeeeeeeeee eeeeee eeeeee eee eeeeeeeee ee eeeeeeeee(MM) eeeeeeeee ee eeeeeeeee(8) eeeeeeeee ee Meeee M′ (Meeeee 88), eee eeee eeeeee ee eee eeeeeeeeeeee eeeeee(M) eeeeeeeeee eee eeeeeee ee eeeeeeeee eeeeee ee eee (Meeeee eeeeeeee). Mee eee ee eeeeee ee eeeeeee eee eeee ee e eeeeeeeeeeee, eee ee eee eeeeeeee ee eee eeeeee.
Meeeeeeee eeeeeeeeee eee eeeeeeee eeeeee eee Meeeeeeeeee eeeeeeee eeeeeeeee eeeeeee eee eeeeeeeee(8) eeeeeeeee eee eeeeeeee ee eee, eeeeeeee eee ee eee-eeeeee eeeeeeeeeeeeeee eeeeeeeee eeeeee eeee eeeeeeee ee ee eeeeeeeee ee eee eeeeeee eeeeeeeeee (Meeeeeeeeee eeeeeeeee ee eeeee, eee eeeeee-eeee eeeeeeeeeeee ee eeee eeeeeeee eee eeeeeeeee ee Meeeeeee 88.8.8.8.8.8 eee 88.8.8.8.8, eeeeeeeeeeee.)
Me ee eeeee eeee eee eeeeeeee eeeeeeeeee ee eeeeeee eeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeeee ee M8Me < M8Me ≈ M8MMe < M8M, eeeeeeeeee eeeee eeeeeeeeee eeeeee eeeeeeeee eeeeeeee. Meeeeeee-eeeeeeeeeee eeeeeeeeeeee ee eeeeeeee eeeeeee eeeeeeee eeeee eeeeeeee eeee, ee eeee eee eeeeeeeeee eeeeeee ee eee eeeeeeeeee eeeeeeee (eeeeeeeeeeeeee eee eeee eeeeeeee eeee eeeeeeeeeeeeeee).
Meee eeeeeeee ee “eeeeeeeee” Meeeeeeeeee eeeeeeeeee eee ee eeeee ee eee eeeeeeeeee. M eeeeeee eeeeeee eee eee eeeeeeeee ee M,M-eeeeeee-8-(eee-8-eeee)eeeeeeee 88 eeee eeeeeee 88 ee eeeee ee Meeeee 88.[88]
Meeeee 88 Meeeeeeee ee M,M-Meeeeee-8-(eee-8-eeee)eeeeeeee Meeee “Meeeeeeee” Meeeeeeeeee Meeeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
M,M-Meeeeee-8-(eee-8-eeee)eeeeeeee 88; Meeeeee Meeeeeeee:[88]
Me e eeee ee Me8M (88.8 eM), [MeMe8(MMe8)8] (8.888 e, 8 eee%), M,M-eeeeeee-8-eeeeeeeeeee 88 (8 eeee), eee e eeeeeeee eeeeeeeee (8.8 eeee, eeeeeee 8 eee eeeeeeeeee), eee eeeee MeM (8.888 e, 8 eee%) eee eeeeeeee eee eeeeeeeee eee eeeeeee 8 eee eeeeee eeeeeeee eeee eeeee. Mee eeeee eee eeee eeeeee. Mee eeeeeee eee eeeeeee ee eeee ee ee eeeee eee eeeeeeee eeeeeeeee eee eeee eeeeeeee eee eee eeeeeeeee eeee eee eeeeeeee, eeeeee eeee eeeee, eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee Me8M eeeeeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeee ee eeeee eee eeeee eeeeeee. Mee eeeee eeeeeeee 88 eeee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee).
References
[60] | Meeeeeeeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
[61] | Meeee, M.; Meeeeeeeeee, M.; Meeeeeee, M., Meeeeeeee, (8888), 888. |
[62] | Meeeeeeee, M.; Meeeeeee, M.; Meeeeeeeeee, M.; Meeeeeee, M., Meeeeeeee, (8888), 888. |
[63] | Meeeeeeeeee, M.; Meeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[64] | Meeeeeeeeee, M., M. Meeeeeeee. Meee., (8888) 888, 88. |
[65] | Meeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[66] | Mee, M.; Meeeee, M. M., Mee. Meee., (8888) 8, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8e, 888.