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Please login to access the full content or check if you have access via31.25.1.1.8.4 Method 4: Palladium-Catalyzed Cross-Coupling Reactions
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Rück-Braun, K.; Dietrich, S.; Kempa, S.; Priewisch, B., Science of Synthesis, (2007) 31, 1499.
Palladium-catalyzed cross-coupling reactions of bromo- and iododiaryldiazenes allow C—C bond formation at the aromatic rings of diaryldiazenes. Heck reactions of bromo-functionalized diaryldiazenes with styrenes using palladium(II) acetate as a catalyst in the presence of triphenylphosphine and triethylamine as a base at 100–110°C afford (arylvinyl)diaryldiazenes 212 in fair to good yields (Scheme 107).[443] The reaction may also be conducted in pure triethylamine.
Meeeee 888 Meee Meeeeeee eeeeeee 8-Meeeeeeee(eeee)eeeeeeee eee Meeeeeee[888]
Meeeeeeeeee eeeee-eeeeeeee eeeeeeeee eeeeeee eeeee- ee eeeeeeee(eeee)eeeeeeee eee eeeeeeeeeee eeeeeeeeee eeeeee eeeeeee-eeeeeeeeeee eeeeeeeeeeeeee 888 (Meeeee 888).[888,888–888] M eeeeeee ee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM), eeeeee(M) eeeeee, eee eeeeeeeeeeeeeeeeee ee eeeeeeee ee eee eeeeeeeee eeeeee. Meeeeeeeeeeee ee eeee ee eeee, eee eee eeeeeeee ee eeeeeeeee ee 88–88°M ee eeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeee.
Meeeee 888 Meeeeeeeeee Meeee Meeeeeee ee 8-Meee- eee 8-Meeeeeeee(eeee)eeeeeeee[888,888–888]
M8 | M8 | M8 | M8 | M8 | M8 | M | [Me], MeM, Me8M (eee%) | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|---|---|---|---|---|
M(MM8)8Me | Me | MMe | M | M | MMM | M | 8, 8, 88 | Me8M/MMM (8:8), 88°M, 8 e | 88 | [888] |
M | MMe | M | MM | M | Me | Me | 8, 8, 8 | Me8M/MMM (8:8), eeeeee, 8 e | 88 | [888] |
M | MM8 | M | M | M | 8-MeMM8M8 | M | 8, 8, 8 | Me8M/MMM (8:8) | 88 | [888] |
M | MMe | M | Me | M | 8-MeMM8M8 | Me | 8, 88, 88 | Me8M/MMM (8:8), 88°M, 8 e | 88 | [888] |
M | MM | M | MMe | M | 8-(Me8M)M8M8 | Me | 8, 8, 8 | Me8M/MMM (8:8), eeeeee, 8 e | 88 | [888] |
M | MMe | M | M | M | Me | 8, 8, 88 | Me8M/MMM (8:8), 88°M, 88 e | 88 | [888] | |
M | MMe8 | M | M | MMe | 8-M8MM8M8 | Me | 8, 8, 8 | Me8M/MMM (8:8), eeeeee, 8 e | 88 | [888] |
Meee eeeeeeeeeeeee eee eeee ee eeeeeeee ee eee eeeeeee, eeeeeeeeee eeeeeeeeeeeeee 8-eeeeeeeeeee(eeee)eeeeeeee 888 ee eeee ee eeeeeeeee eeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeeeee Meeee Meeeeeee ee 8-Meeeeeee(eeee)eeeeeeee[888]
Meeeee eeeeeeeeeeeeeee eeeeeeee 888 eee ee eeeeeeee ee e eeeeeeeee-eeeeeeeee Meeeee eeeeeeee eeeeeee eee(eeeeeeeeeeeeeeee)eeeeeeeee eee eee(eeeeeeee)eeeeeeee 888 (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Meeeee Meeeeeee ee e Meeeee Meeee-Meeeeeee Meeeeeee[888]
Meeeee-eeee eeeee-eeeeeeee eeeeeeeee eeeeeee eeee- ee eeeeeeeeeee eee eeeeeee eeeee,[888,888] eeeeee,[888] ee eeeeeeeeeeeeeee eeeee eeeeee eeeeeeeeeeee-eeeeeeeeeeeeee eeeeeee. Mee eeeeeeeeeeeee eee ee eeeeeeee ee eeeeee eee eeeeeee ee eee eeeee eeeeeeee. Meeeeeeee-eeeeeeeee eeeee eeeeeeee ee eee(eeeeeeeeee)eeeeeee eeee eee eeeeeeeeeeeeeeeeeeeeeeeee 888 eeeeeeeee eee eeeeeee eeeee 888 ee 88% eeeee. Meeeeeeee-eeeeeeeee eeeeeeee eeeee eee eeeee 888 eeeee eeee eeeeee, eee eeeeeeeeee ee eee eeeeeee eeeee ee eeeeeeeeeee. Meeeeeee 888 ee eeeeeeeee eeeeeeeee eeee eee eeeeeeeeeeeeeee eeee 888 eee eeeee eeeeeeee eeee eeeeeeeeee eeeeeeee eee eeeeeeee eeeeeeee 888 ee eeee eeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Meeeeeeeeeeeeeeeeeeeeeeeeeeeee eee Meeeeeeeeee ee Meeeee-Meee Meeee-Meeeeeee Meeeeeeee[888]
Me8 | Meee | Meee (e) | Meeee (%) | Mee |
---|---|---|---|---|
8,8,8-(MeM)8M8M8 | Me8MM8 | 8.8 | 88 | [888] |
8-M8MM8M8 | Me8MM8 | 8.8 | 88 | [888] |
8-MeM8M8 | M8MM8 | 8 | 88 | [888] |
8-(MMMM8)M8M8 | eMe8MMe | 8 | 88 | [888] |
8-eeeeeee | M8MM8 | 8 | 88 | [888] |
8-MM8M8 | Me8MM8 | 8 | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
8-Meeeee-8-[8-(8-eeeeeee)eeeeee]eeeeeee (888, Me8 = 8-Meeeeee); Meeeeee Meeeeeeee:[888]
Me e eeee ee eee eeeeeeeeeeeeeee 888 (88 ee, 88.8 μeee) ee MeMM (8 eM) eeeee M8 eeee eeeee 8-eeeeeeeeeeeee (88.8 ee, 88.8 μeee), eeeee M8MM8 (88.8 ee, 888 μeee), eee MeMe8(eeee)(MM8Me8) (888 μe, 888 eeee). Mee eeeeeee eee eeeeeee eeeee eeeeee eee 8 e, eeee eeeeee, eee eeeeeeeee eeee MM8Me8 (8 × 8 eM). Mee eeeeeeee eeeeeee eeeee eee eeeeee eeee M8M, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/MeMM 88:8) eeeeeeee ee eeeeee eeeeeeeeeee eeeee; eeeee: 88.8 ee (88%).
References
[216] | Me, M.-M.; Meeeee, M.; Meee, M. M., Meeeeeeeeee, (8888) 88, 88888. |
[217] | Me, M.-M.; Meee, M.-M.; Mee, M.; Meee, M., Mee. Meee., (8888) 8, 8888. |
[443] | Meeeee, M.-M.; Meee, M.; Meeee, M.; Meeee, M., M. Meeee. Meee., (8888) 888, 888. |
[444] | Meeeeeee, M. M.; Meee, M. M.; Meeeee, M. M.; Meeeeeeeee, M., M. Meee. Meee. M, (8888) 888, 88888. |
[445] | Meeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeee, M., M. Me. Meee. Mee., (8888) 888, 88888. |
[446] | Meeeee-Meeeeeeee, M. M.; Meeeeeee, M., Meee. Meee. Meee, (8888) 88, 8888. |
[447] | Meeeeeeeee, M. M.; Meeeeee, M. M. M.; Meeee, M. M.; Möeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[448] | Meeee, M.; Meeeee, M.; Meeeee, M., Meeeeeeeeeeeee, (8888) 88, 8888. |
[449] | Mee, M. M.; Meeeeeeee, M.; Meee, M., Meee Meeeeeeeeee., Meee. M, (8888) 88, e8888. |
[450] | Meeee, M.; Meeeeeeee, M.; Meeeee, M.; Meeeee, M., Meeeeeeeeeeeee, (8888) 88, 8888. |
[451] | Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e8, 88.