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Please login to access the full content or check if you have access via9.10.1.4.4.4.3 Variation 3: Palladium-Assisted Coupling Reactions
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Schatz, J., Science of Synthesis, (2001) 9, 388.
Iodo- or bromothiophenes react with terminal alkenes[1087–1089] or alkynes[1053,1090,1091] under catalysis by palladium(0) in a Heck-type coupling to give (alk-1-enyl)- or (alk-1-ynyl)thiophenes;[1090,1092–1094] examples are given in Scheme 128. Sometimes, stoichiometric amounts of palladium(0) are necessary.[1088,1091,1095] In mixed bromoiodo-substituted thiophenes, the more reactive iodine atom is replaced selectively.[1096] Reaction without palladium catalysis but under photochemical conditions is possible, as shown by the synthesis of 1-nitro-5-(phenylethynyl)thiophene (87%) from 1-iodo-5-nitrothiophene and phenylacetylene.[771]
Meeeee 888 Meee-Meee Meeeeeee Meeeeeee ee 8-Meeeeeeeeeeeee
eeee Meeeeeee Meeeeee[8888,8888]
M | M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|
M | M | Me | (Me8M)8Me, MeM, Me8M | 88 | [8888] |
M | M | Me | (Me8M)8MeMe8, MeM, Me8M, M8MM8 | 88 | [8888] |
Me | M | Me | (Me8M)8Me, MeM, Me8M | 88 | [8888] |
M | M | Me | (Me8M)8Me, MeM, Me8M | 88 | [8888] |
Me | M | Me | (Me8M)8Me, MeM, Me8M | 88 | [8888] |
M | M | MM8MMMM | (Me8M)8Me, MeM, Me8M | 88 | [8888] |
M | M | MM8MMMM | (Me8M)8Me, MeM, Me8M | 88 | [8888] |
M | 8-eeeeeee | Me | (Me8M)8Me, MeM, Me8MeMMe, 8.8 M MeMM | 88 | [8888] |
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeeeeeeeee 888; Meeeeee Meeeeeeee:[8888]
Me e 888-eM, eeeee-eeeeeeee eeeee eeeeee eeee M8 eeee eeeee Me8M (88 eM), eee eeeeeeee eeeeee (88–88 eeee), eeeeeee (88 eM), 8-eeeeeeeeeeeee (8.88 e, 88.8 eeee), (Me8M)8Me (888 ee, 8.8 eeee), eee MeM (88.8 ee, 8.8 eeee) ee ee. Meeee 88 e, MeMM (88 eM) eee eeeee, eee eeeeeee eee eeeeeeeeee, eee Me8M (888 eM) eee eeeee ee eee eeeeeeeee eeeeeee, eeeeeee ee eee eeeeeeeeeeeee ee Me8MM+M−. Meee eeeeeee eee eeeeeeee, eeeeee eeee 88% MMe, M8M, eee eeeee, eee eeeee (MeMM8 ee Me8MM8). Mee Me8M eeee eee eeeeeeeeeee eeee eeeeeeeee eeeeeeee eee eeeeeeeeee; eee eeeeeeeee eeeeeee eee eeeeeee eeeeeeee ee Meeeeeeee eeeeeeeeeeee ee eeee 888; eeeee: 88–88%.
References
[771] | M'Meeee, M., Meee. Meee. Meee., (8888) 888, 888. |
[1053] | Meeeeeee, M. M.; Meeeeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 888. |
[1087] | Meeee, M. M.; Mee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[1088] | Meeee, M.; Meee, M.; Meeeeee, M.; Meeee, M., Meee. Meee., (8888), 888. |
[1089] | Mee, M.; Meeee, M.; Meee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[1090] | Meeee, M. M.; Meee, M. M., M. Meeeeeeee. Meee., (8888) 88, 888. |
[1091] | Meeee, M.; Meeeeee, M.; Meeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[1092] | Meeeeeee, M. M.; Meeeeeeee, M.-M., Me Meeeeee-Meeee Meeeeeeeeeeeee Meeeeeeee, Meeeeee, M.; Meeeeeee, M. M., Mee.; Meeee-MMM: Meeeeeee, (8888); e 888. |
[1093] | Meee, M. M., Mee. Meeee. (M. M.), (8888) 88, 888. |
[1094] | Meeeeee, M., Meeeeeeeeee, (8888) 88, 88888. |
[1095] | Meee, M.-M.; MeMeeeeee, M. M., M. Meeeeeeee. Meee., (8888) 888, 888. |
[1096] | Meeeeeeee, M.; Meeeee, M., Meee. Mee., (8888) 88, 888; Meee. Meeee., (8888) 888, 88888. |
[1097] | Mee eee Meeee, M. M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
[1098] | Meeeeee, M. M.; Meeeeeeeeeee, M.; Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.