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Vaultier, M.; Alcaraz, G., Science of Synthesis, (2005) 6, 837.
The metal-catalyzed cross coupling of alkenylboranes and electrophiles is a convenient methodology used in organic synthesis for the formation of C—C bonds. The cross coupling can be performed with or without the loss of boron. First reported in 1993,[372] alkyl- or vinylzinc chlorides can be coupled, in the presence of a palladium catalyst, with (2-bromvinyl)boronates leading to the corresponding isolable alkylated or vinylated homologues 256 or 257, respectively, without loss of boron (Scheme 129).[372,373]
Meeeee 888 Meeee Meeeeeee ee 8-Meeeeeeeeeeeeeeeeee eeee Meeee- eee Meeeeeeee Meeeeeeee[888,888]
Meee eeee ee eeeeeeee ee eeeeee Meeeeee eeeee eeeeeeee, eee eee eeeeeeee ee e M—M eeee eeeeeeeee eeeee eeeee eeee eee eeee ee eeeee eee eeee ee eeeee eeeeee ee Meeeee–Meeeeee eeeee eeeeeeee. Mee eeeeee eee eeee eeeeeee eeeeeeeeeee eee eeeeeeee.[888] Meeeeee eeee eeee eeeeeeeeeeeeee[888,888] eeee eeeee eeeeeeeeeeeee, eeeeeeeee eeee[888] ee eeeeeee eeeeeee,[888] eee eeeeeeeeeeeeeeeeeeeeeeeeee[888,888] Meeeeee eeeeeee eeeeeeeeee ee eee eeeeeeeee eeeeeeeee ee eee eeeeeeee eeeeeeeee. Mee eeeeeee, e eeee eeeee ee eeeeeeeeeeeeeeee eeeeeee eee eeeeee eeeeeeeeeeeeee eeeeeeeeeeeee eee eeeeeee eeeeeeeee. Mee eeeeeeeeeeeeee eeeeeeeee ee eeeeeee eeeeee ee eeeeeeee eeeeee eee eeeeeeee, eee eeeeeee eeeeeeee, eeeeeeeee eeeee ee eeeee eeeeeee, eee ee eeee. Mee eeeeeeeee ee eee eeeeeeee eeeeeeee eeeeeeee eeeee eeee eeeee: eeeeeeeee eeeeeeee, eeeeeeeeeeeeeee, eeeeeeeee eeee eeeeeeeeeeeee, eee eeeeeeeee eeeeeeeeeee. Meeeeeeee eeeeeeee ee eee eeeeee eeeeeeeee(8) eeeeeeee ee eeeee eee eeee-eeeeeeeeeee eeee eeeeeee ee ee eeeeeeeeeeeeeee(MM) eeeeee eeeeeeeeeeee. Meeeeeeeeeee ee eee eeeeee ee eeeeeeeeeeeeeee eeee eee eeeee eeee ee eee eeeeeeeee(MM) eeeeee eeeeeeee e eeee eee eeeeeeee ee “eee” eeeeeee eeee eeeeeeeeeee eee eeeeeeee ee ee eeeeeee eeeee eeee eeeee ee eeeeeeeee(MM). Meeeeee, eeee eeeeeeeee (ee eeeeeee) eee eeeeee ee eeeeeeee eeeeeeeeeee eeeeee e (eeeeee)eeeeeeeee(MM) eeeeeeeeeeee eeee eeeeeee eee eeeeeeeeeeee eeeeeeeeeeeeeee eeee eeeee ee eee eeeee eeee. Meee ee eeeee eeeeeeeee eee eeeeeeeee eee eeeee eee eeeee eeeeeeeeee. Mee M—M eeee ee eeeeee ee eee eeeee eeeeeeeee eeeeeeeeeee eeee eee eee eeeeeeeee(8) eeeeeee ee eeeeeeeeeee. Mee eeeeeeeee eeeeeeeeeee eeeeeeee eeee eee eeeeeee eee e eee-eeeeeeeeeeeee, eee ee ee eeeeeeeee ee ee eeeeee ee eeeeeeeee (Meeeee 888).[888,888]
Meeeee 888 Meeeeeeee Meeee eee eee Meeeeeeee-Meeeeeeee Meeee Meeeeeee ee Meeeeeeeeeee[888,888,888]
Meeeeeeee, eeeeeeeeeeee eeeee eee eeeeee eeeeeee eeeeeeee ee eeee eeeeee. Meee eeeeeee(eeeee)eeeeeee, eee eeeeeeee eee ee eeeeeeeeeee ee eeeeeeeeeeeeeeeee eee eee eeeeeeeee ee eeee-eeeeeeee. Mee Meeeee–Meeeeee eeeee-eeeeeeee eeeeeeeee ee M- ee M-eee-8-ee-8-eeeeeeeee, eeeeeeeee, ee eeeeeee eeeee eeee M- eee M-eee-8-ee-8-ee eeeeeee eee eeee eeeeee- eee eeeeeeeeeeeee, eeeeeeeee e eeeeeee eeeee ee eeeeeeeeeeeeeeeee eeee-eeeeeee eeeeee.[888–888] Mee eeeeeeeeeee ee eeee eeeeee eee eeee eeeeeeeeeee eeee eee eeeeeeeee ee eeeeeeee (888) (eee eeeeeeeee ee eee eeee eeee Meeeee eeee) eee eee eeeee eeeeeeeee eeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Meeeeeee eee Mee Meeeeeeee Meeeeee eee Meeeee–Meeeeee Meeee Meeeeeee[888]
Me eee eeeeeeee eeeeeee ee eee eeeee-eeeeeeee eeeeeeee,[888,888] eeeeee eeeeeeeee ee eeeeeeeee eeeeeeeee eeee eeee ee eee eeee. Meeeeee, eee eeeeee ee eee eeee eee e eeeeee eeeeee ee eee eeeeeee ee eee eeeeeeee. Meeeeeee eeeeeeeee eeeeeeeeeeeee eeeeeeee eee eeee ee eeeee eeeeeeee, eeeee eee eeee ee eeeeeee eee ee eeee eeeeeeeeeee ee eeee ee 8°M. Meee eeeeeeeee eee eeeee eeeeeeee eee eeee ee eee eeeeeeeee ee eeeeeeeee,[888] eee eeeee eee eeeee eeeeeeeeeeee eeeeeeeeeee eeeeee.[888–888] Meeeeeeeeeee eeee eeeeeee eeeeeeee eeee 8-eeeeeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8) eee e eeee eeee ee eeeeee eeeeeeeee ee eeeeee eeeeeeeee ee eeee eeeeee 888 (Meeeee 888).[888]
Meeeee 888 Meeeee–Meeeeee Meeee Meeeeeee ee Meeeeeeeeeee eeee 8-Meeeeeeeeeee[888,888]
M8 | M8 | MM8 | M8 | Meeeeee (%) | Meeeee (%) | Mee |
---|---|---|---|---|---|---|
Me | M | MMee8e | (MM8)8Me | 88 | 88 | [888] |
Me | M | MMee8e | Me | 88 | 88 | [888] |
Me | M | MMee8e | (MM8)8Me | 88 | 88 | [888] |
Me | M | MMee8e | Me | 88 | 88 | [888] |
M | Me | MMee8e | (MM8)8Me | 88 | 88e | [888] |
Me | MMe | 8-MMM | Me | 88 | 88e | [888] |
e Meeeeeee eeeeee eeeeeeeeee ee MM.
e Meeee eeeee ee eeeeeeeeeee eeee eee eeeeeeeeee ee MM.
e Mee = 8,8-eeeeeeeeeeeeee.
e 88% Meeeee ee eeeeeeeeeeeee eee 8 eee% ee eee eeeeeeee eeee eeee.
e MeMM eee 8 eee% ee eee eeeeeeee eeee.
Meeeeeeeeeeeee eeeeeee eeeeeeee eeee eeeeeee eeeeeee,[888] 8,8-eeee-8,8-eeeeee eeeeeeeeee eeeeeeeee eeeeee,[888] ee eeee ee eeeeeeeee eeeeeee eeeeeeeeeeee eeeeeeeee eeee eeeeeee eeeeeeeeee[888] ee eeeeeeeeee.[888] Mee eeeee eeeeeeee eee ee eeee eeeeeeeee ee e Meeeeee–Meeeee eeeeee eeeeeeee ee eee eee ee eeeeeee(8-eeeeeeeeee)eeeeee[888] ee eeee (β-eeeeeeeeee)eeeeeeeee 888, eeeee eeeeee e eeeee ee eeeeeeee eeee eeeeeee eeee eeeee eeeeeee, eeeeeeeeeee, eeee ee eeeee eeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeee–Meeeee Meeeee Meeee Meeeeeee eeee (β-Meeeeeeeee)eeeeeeeee[888]
Mee eeeeee Meeeeee eeeeeeee eee ee eeeeeee eeeeeeee; eeee, eeeee e eeeee eeeeee eee eeeeeeee ee e eeeeee eeeeee ee eeeeeeeee eeeeeeee, eee e eeeeeeeeeeeee Meeeee–Meeeeee eeeee eeeeeeee eeeee e eeeeee eeeeeeee eeeeeeeeee, eeeee ee eee eeeeeeeeeeeee β-eeeeeeeeeee α,β-eeeeeeeeeee eeeeee ee eeeeee ee eeee eeeeee.[888] Me eee eeeeeeee ee eeee ee eeeee eeeeeee, eeeeeee eeeeeeeeeeeeee eee eeeee eeee eeeeeeeee eeeeeeeee ee eeeeee eee Meee ee Meeeee–Meeeeee eeeee-eeeeeeee eeeeeeeeee eeeeeeeee eeeeeeeeeeeee eeeeeee eeeeeeeee ee eeeeeee, eeeeeeeeeeee (Meeeee 888).[888,888] Meeee ee eee eee eeeeee ee eeeee eeeeeee eeee eeeeeee eee eeeeee eeeeeeeee(8) eeeeeee eeee eeeeee eee eeeeeee eeee ee eeeeeee eeee eee M—M eeee ee eee eeeeeeeeeeeee. M eeeeeeee eeeeeeeee ee eeeeeeeeee ee Meeeee 888. Mee eeeeee ee eee eeeeeeee eeeeee ee eeee eeeeeeee eeeeeeeee eeee eee eeeeeeee eeeeeeeeee. Meee eeeee eeeeeee ee eee eeeeeee eeeeeeeeeeeee eee eeeeeeeeeeeee eeeeee eeeeeeeee eeee eee Meee eeeee eeeeeeee eee ee eeeeeeee eeeeeeeeeeeeeeee, eee ee eee ee eeeeee eeeeee.[888]
Meeeee 888 Meee eeeeee Meeeee Meeee Meeeeeee ee Meeeeee Meeeeeeeeeeee eeee Meee ee Meeee Meeeeee[888–888]
References
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[215] | Meeee, M.; Meeee, M.; Meeeeeeee, M., Meee. Meee., (8888), 8888. |
[236] | Meeeeeee, M.; Meeeeeeee, M.-M.; Meeeeee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[265] | Meee, M.; Meeeee, M. M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 8888. |
[372] | Meee, M.; Meeeeeee, M.; Meee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[373] | Meeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[374] | Meeeeee, M.; Meeeee, M., Meee. Mee., (8888) 88, 8888. |
[375] | Meeeee, M., Meee Meee. Meee., (8888) 88, 888. |
[376] | Meeeeeeeee, M. M.; Meeeeee, M. M., Meeeeee, (8888), 88. |
[377] | Meeeeeee, M. M.; Meeeeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[378] | Mee, M.; Meeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[379] | Meeee, M. M.; Meeeeeeeee, M., Meeeeee Meeeeeeee eee Meeeeee, Meeeeee Meeeeeee Meeeeee: Meeeeeeee, Meeeeeeee, (8888); e 888. |
[380] | Meeeeeee, M.; Meeeeee, M., Me Meeeeeeeeeeee Meeeeeeeeeeeee Meeeeeeee MM, Meee, M. M.; Meeee, M. M. M.; Meeeeeeee, M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 88, e 888. |
[381] | Meeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 888. |
[382] | Meeeee, M.; Meeeeee, M. M., Mee. Meee. Meee., (8888) 888, 88. |
[383] | Meeeee, M., Mee. Meee. Meee., (8888) 888, 88. |
[384] | Meeeee, M., Meee Meee. Meee., (8888) 88, 8888. |
[385] | Meeeeee, M.; Meeeeeee, M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[386] | Meeeeee, M.; Meeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
[387] | Meeeeee, M.; Meee, M.-M.; Meeeeeeee, M. M.; Meeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[388] | Meeee, M. M.; Meeee, M. M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[389] | Meeee, M. M.; Meeeeeee, M. M.; Meeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[390] | Me Meee, M. M.; Meeeeee, M.; Meeeeeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[391] | Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeeeeeeee, M. M., Meeee. Meee., (8888) 888, 888; Meeee. Meee. Mee. Me. Meee., (8888) 88, 888. |
[392] | Meeee, M. M.; Meee, M.; Meee, M. M.; Meeeeeeeeeee, M. M.; Meeee, M. M., Mee. Meee., (8888) 8, 8888. |
[393] | Meeeeeee, M.; Mee, M.; Meeeeee, M.; Meeeeee, M.; Meee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[394] | Meeeee, M.; Meeeeeee, M.; Meeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[395] | Meeeeeeee, M.; Meeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
[396] | Meeee, M.; Meeeeeeee, M.; Meee, M.; Meeeee, M., Meee. Meee., (8888), 888. |
[397] | Meeeeeeee, M.; Meeee, M.; Meee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[398] | Meee, M. M.; Meeeeee, M. M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[399] | Meeeeee, M. M.; Meeeeee, M., M. Meeeeeeee. Meee., (8888) 888, 888. |
[400] | Meeeeee, M. M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8e, 888.
- 8.Meeeee-Meee, (8888) 88/8e, 888.
- 8.Meeeee-Meee, (8888) 88/8e, 888.
- 8.Meeeee-Meee, (8888) 88/8e, 888.