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Negishi, E.-i.; Takahashi, T., Science of Synthesis, (2003) 2, 795.
The C—C bond formation reactions of alkynes or alkenes with Grignard reagents catalyzed by zirconium(II)–alkene complexes can be classified into seven types of reactions as shown in Scheme 151. The first type is the ethylmagnesation of alkenes (Dzhemilev's reaction)[193,358] or alkynes,[366] e.g. to give 413 and 414, respectively (see also Section 2.11.8.8), the second type is the cyclomagnesation reaction of dienes, e.g. to give 415,[362] and the third is the cyclodimagnesation of dienes, e.g. to give 416.[362] The cyclodimagnesation reaction products are very often obtained together with the ethylmagnesation or cyclomagnesation products. The fourth type of reaction is ethylation of allylic compounds, such as the reactions of 417 and 419 to give 418 and 420, respectively.[367–369] The fifth type is the formation of cyclobutenes such as 421.[370] The sixth is the cycloallylation reaction, e.g. to give 423 from 422, which is a combination of cyclomagnesation and C—C bond formation of allylic compounds.[372,373] The seventh is alkylation of styrenes, e.g. formation of 424.[371]
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Meeeee 888 Meeeeeee Meeeeeee ee Meeeeeeee(MM)-Meeeeeeee M—M Meee Meeeeeeeee ee Meeeeee ee Meeeeee eeee Meeeeeee Meeeeeee[888,888,888,888,888,888–888]
Mee eeeeeeeeeeeeeeee eeeeeeee ee eeeeeee (Meeeeeeee'e eeeeeeee) eee eeeee eeeeeeee ee 8888;[888] eee eeeeeeee eeeeeeeee ee eeeeeeeee ee Meeeeee 8.88.8.8 eee eeeee ee Meeeee 888. Mee eeeeeee ee eee eeeeeeee eeee eeeeee eeeeeee ee eeeeeee, e.e. 888 ee 888, eeeeeeeeeeee, ee eee eeeeeeee eeeeeee ee ee eeeee eee ee MeM eeeee ee eee M=M eeee ee eee eeeeeeeeeee eeeeeeee eeeeeeeee (Meeeeee 888 eee 888).
Mee eeeeeeeeeeeeeeee eeeeeeee ee eeeeeeeeee ee eeee eeeeeee eeeee eeeeeeeeee eeeeee eeeeeeee ee eeeeeeeeeee eeeeeeeeeee ee eeee eeeeeeeeeeeeeeeeeeeeeee, eeeee ee eee eeeeeee eeeeeee eeeeeeeeeeeeeee eeee eeeeeeeeeeeeee eeeeeee. Meeeeeeeeeeee, eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeee ee eeeeee 888 eeee eeeee,[888] eeeeeeeeee eeeeeee eeeeee ee eee eeeeeeee ee eee(η8-eeeeeeeeeeeeeeee)eeeeeeeee(MM) eeeeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee ee Meeeee[888]
Meeeee 888 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee Meeeeeeeee Meeeee[888]
Mee eeeeeeeeeee ee e eee(η8-eeeeeeeeeeeeeeee)eeeeeeeee eeeeeee eee ee eeeeeeeeeeeeee eeeeee eee eeeeeeee eeeeeee eeeee eeeee ee eeeeeeeee eeeeeeeee. Me eeeeeee, eeee ee eeeeeeeeeeeeee eeeeee ee eeee, ee eeeee ee ee eeeeee eeeee ee eeeeeeeeee eeee eee eeeeeee ee eeeee eeeee. Meeeeee, e eeeee eeeee ee eee eeeeeeeeee ee eeeeeeeeeeeeee eeeeeeee ee eeee eeeeeee; eeeeeeeee, eee eeeeeeeeeee ee eeeeeeeeeee(η8-eeeeeeeeeeeeeeee)eeeeeeeee(MM) eeee eeeeeeeeeeeeee eeeeeeee ee eeeeee eee eee eeeeeeeee eeeeeeeeeee ee eeeeee ee eeeeeee eeeeeeeee.[888,888–888]
Mee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeeee ee eeeeee ee eeeeeeee eeeeeee. Me eee eeeeeeee eeee eeeeeeeeeeeeee eeeeeee, eee eeeee 888 eeeeee eeee ee eee eeeeeeee eeeeeeee eeeeeee ee eeee 888 eee eeeeeeee 888. Me eeeee eeeeeeee, eee eeeeeeee eeee e eeeeeeeeeeeeee eeeeee eeeeeeeee e eeeeee eeeeeee ee eeee 888. Meeeeeeee ee eee eeeeeeee eeeeeeeeee, eeeeee eee eeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeeeeeee eee ee eeeeeeee.[888,888–888] Meee eeeeeeee eee eeee eeee eeee ee eee eeeeeeeee ee 888 eeee eeeeee 888 (Meeeee 888).[888]
Meeeee 888 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee Meeeee[888,888]
Mee eeeeeeeee-eeeeeeeee eeeeeeeeee (ee eeeeeeeeee) ee eeeeeee eeeeee eee eeeee eeeeeeeeeee ee eeeeeeeee eeee eee eeeeeeeeeeeeeeee eeeeeeee eeeeeeeee eeeee ee ee eeeeeeee eee eeeeeeeeeee ee e eeeeeee eeeee eee eeeeee-eeee eeeeeeeee. Me eeee eeeeeeee, M—M eeee eeeeeeeee eeeeee ee eee eeeeeee eeeeee eee eee MeM eeeeee ee eee eeeeeeeeeeee ee eee eeeeeee; eee eeeeee eeeee eeeeeeee eeee eee MeM eeeee.[888] M eeeeeeeeeee eeeee ee eeee eeeeeeee eee eeeeeeee eeee eee eeeeee eeeee ee eee eeeeeee eeeeee eeeeee eeeeeeeeee eeeeeee eee eeeeeeeee ee eee Me—M eeee. Me eee eeee ee 8,8-eeeeeeeeeeee eeeeeeee eeee eee eeeeee eeeeeeee ee eeeeeeeeeeeeee eeeeeee eeeeeeee eee e Meeeeeeee-eeee eeeeeeee ee eeeeee eee eee Me—M eeee. Mee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeeeee eeeeee eeeee ee eee γ-eeeeeeee ee eeee 8-eeeeeeee-8-eeee (Meeee 88).[888] Me eee eeee ee eee eeeeeeeeee eeeeeeee ee eeeeeeee eeee ee eeeee eeeeee ee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeeee (e.e., ee eeee 888, Meeeee 888), eee eeeeeeeee ee e eeeeeeeeeeeeeee eeeeeeeeee ee eee eee eeee; eeee eeeeeeee ee eeeeeeeee ee Meeeeee 8.88.88.8.[888]
Me e eeeeeee eeeeee ee eeee eeeeeeeee eeeee, eeeeee eeee ee 888 eee 888, ee eeeee eee ee eee eeeeee eeeee ee eeee ee ee eeeeeee eeeee eeeeee, eee eeeeeee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeee eeeeeeee ee eeee eeeeeeeee 888 eee 888, eeeeeeeeeeee (Meeeee 888).[888–888]
Meeee 88 Meeeeeeee(MM)-Meeeeeeee Meeeeeeeee ee Meeeeee Meeee Meeeeeeeeee[888]
| Meeeeee Meeee Meeeeeeeee | Meeeeeeeeee ee MeMeMe | Meeeeee | Meeee (%) | Mee |
|---|---|---|---|---|
 |
8 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
8 | |
88 | [888] |
| |
8.8 | |
88 | [888] |
| |
8 | |
88 | [888] |
Meeeee 888 Meeeeeeee(MM)-Meeeeeeee Meeeeeeeeeeeeee[888–888]
| M | M | Meeeee (%) ee 888 | Mee |
|---|---|---|---|
| MM8 | MMe | 88 | [888] |
| MM8 | MMe | 88 | [888] |
| MMe | MMe | 88 | [888] |
| MMe | MMe | 88 | [888] |
e eee/eeeee eeeeeeee.
Mee eeeeeeeee ee eeeeeeeeeeee ee eee eeeeeeeee-eeeeeeeee eeeeeeee ee eeeeeee eeeeeee eeee eeeeeeeeeeeeee eeeeeee ee ee eeeeeeeeeee eeeeeee ee eee eeeeeeeee eeeeeeee ee e eeeeeeeee(MM)–eeeeee eeeeeee eeee eeeeeee eeeeeee ee eeeee eee eee M—M eeeee eee eeeeee ee eeee eeeeeee ee eeeeee, e.e. eeeeeeeee ee 888 eeee 888 (Meeeee 888).[888] Mee eeeeeeeee ee eeee eeeeeeeee eeeeeeee ee eee eee eeeee; eeeeeee, eeeeeeeee eeeeeeeeeee ee ee eeeeeeeeeeee eeeeeeeeeeeeeeeeeee ee eeeeeeeeee.[888] Mee eeeeeeeeeeeeee eeeeeee ee eeee eeeeeeee eeeee eeeeeeeeeeeeeeeeeeeeeee eeeeeeeeeee eeee eee ee eeeeeeeee eeee 888 eee 888 eeee eeeeeeeeeee eee eeeeeeeeeeee, eeeeeeeeeeee.
Meeeee 888 Meeeeeeee(MM)-Meeeeeeee Meeeeeeeeee Meeeeeeee[888]
Meeeeeeee(MM)-eeeeeeeee eeeeeeeeeeeeeeee eeeeeeeeeeeeeee eeeeeeeee eeee eeee eeeeeeeee eee (e) eeeeeeeeeeeeeeee ee eeeeeee, (ee) eeeeeeeeeeeeeeee ee eeeeee, eee (eee) eeeeeeeeee (ee eeeeeeeeee) ee eeeeeee eeeeeeeee ee eeeee Meeeeeeeeee eeeeee eeeeeeeeeee eeeeeeeeeee ee e eeeeee (η8-eeeeeeeeeeeeeeee)(eeeeeeeeeeeeeeeeeeeeeeeeeee)eeeeeeeee eeeeeee.
M eeeeeeeeee eeeeeeeeeeeeeeee eeeeeeeeeeeeeeee ee eeeeeee eee eeee eeeeeeee eeeee eee eeeeeeee 888. M-Meeeeeeeeeee (888) eeeee eee eeeeeeeeeeeee eeeeeeeeeeeeeeee eeeeeee 888 ee 88% eeeee eee eeee ee eeeeeeeeeeee eeeeee ee 88%.[88] Me eeeeeeee, eee eeee eeeeeeee eeee eee (M)-8,8′-eeeeeeeeee-8,8′-eeeee [(M)-MMMMM] eeeeeee 888 eeeeeee 888 ee eeee 88% eeeee eeee 88% eeeeeeeeeeee eeeeee (Meeeee 888).
Meeeee 888 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeee Meeeeeeeeeeeeeee ee Meeeeee[88]
Meeeeeeeeeeeeeee eeeeeeeeeeeeeeee eee eeee eeeeeeeee eeee eee Meeeeeeeeee eeeeee eeeeeeeee eeeeeee 888. Meeeeeeeee, ee eee eee ee eee eeeeeeee ee eeeeeeeeeee 888 eee 888 eeee eeeeeeeeeeeeee eeeeeeee ee eeee 888 eee 888, eeeeeeeeeeee. Meeeeeee eee eeeeeeee eeeeee eee eeeeeeeee eee (<88%), eee eeeeeeeeeeee eeeeee ee eeee 88% (Meeeee 888).[888]
Meeeee 888 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeee Meeeeeeeeeeeeeee ee Meeeee[888]
Mee eeeeeeeeeeeeeeee eeeeeeeeee ee eeeeeeeeee ee eeeeeee eeeeeeeee, eeee ee 888, 888, eee 888, eeeee eeeeeeeeeeee eeeeeeee eeeeee eee eeeeeeeeeeeeeeeeee eee eee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee, e.e. 888, 888, eee 888, eeeeeeeeeeee. Meeeeee, eee eeeeee ee eeeeee eeeeeeeeee eeeeeeee eeeeeeee eeee eeeeeeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeee eee ee eee 88–88% eeeee, e.e. eeeeeeeee ee 888 eeee 888 (Meeeee 888).[88,888,888] Meee eeeeee eeeeeee eeeeee, e eeee eeeeeeeeeeee eeeeeeeee-eeeeeeeee eeeeeee eeeeeeeeee eee eeee ee eeeeeeee eeeee 88 eee% ee (M)-88 eee 8 eeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeee (Meeee 88).[888,888]
Meeeee 888 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeee Meeeeeeeee ee Meeeeeeeee ee Meeeeee Meeeeeeee[88,888]
Meeee 88 Meeeeeeee-Meeeeeeee Meeeeee Meeeeeeeeee ee Meeeee Meeeeee Meeeee[888,888]
| Meeeeee Meeeeeeee | Meeeeeeeee (%) | ee (%)e | Meeeee | Mee |
|---|---|---|---|---|
| |
88 | 88 | M | [888,888] |
| |
88 | 88 | M | [888,888] |
| |
88 | 88 | M | [888,888] |
| |
88 | 88 | M | [888,888] |
| |
88 | 88 | M | [888,888] |
e Meeee 88 eee% (M)-88 eee MeMeMe (8 eeeee).
e Meeeeeeeeeee eeeeee ee eeeeeeeee eeeeeeeee.
References
| [58] | Meee, M.; Meeeee, M. M.; Meeee, M. M. M.; Meeeeee, M. M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [193] | Meeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 888; Meee. Meee. Mee. MMMM, Mee. Meee. Mee. (Meee. Meeeee.), (8888) 88, 888. |
| [355] | Mee, M.; Mee, M.-M.; Meeeeeee, M.; Meeeeeeee, M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |
| [358] | Meeeeeeee, M. M.; Meeeeeeeee, M. M., M. Meeeeeeee. Meee., (8888) 888, 88. |
| [362] | Meeeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [366] | Meeeeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [367] | Meeeee, M.; Meeeeeee, M. M.; Meeeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [368] | Meeeeeeee, M.; Meeeeeee, M. M.; Meeeee, M., Meee. Meee., (8888), 888. |
| [369] | Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [370] | Meeee, M.; Mee, M.; Meee, M.; Meeeeeeee, M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |
| [371] | Meeee, M.; Meeeeeee, M.; Meeee, M.; Meeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [372] | Meeeee, M. M.; Meeeeeee, M. M., Meeeeeeeeeeeeee, (8888), 88, 8888. |
| [373] | Meeeeeeee, M.; Meeeeeee, M. M.; Meeeee, M., Meeeeeeeeeeeeee, (8888) 88, 8888. |
| [374] | Meeeeeeee, M.; Meeeee, M.; Meeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
| [375] | Meeeeeeeee, M.; Meeeee, M. M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [376] | Meeeee, M.; Meee, M.; Meeeeee, M.; Meee, M., M. Mee. Meee. (8888) 88, 8888. |
| [377] | Meeeeeeeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [378] | Meeeeee, M.; Meeeeee, M. M.; Meeeeeee, M.; Meee, M. M.; Meeeee, M.; Meeeeeeee, M., Meeee. Meee. Meee, (8888) 888, 8. |
| [379] | Meeeee, M. M.; Meee, M.; Meeeeeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [380] | Meeeeee, M.; Meeeeeeee, M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [381] | Meeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [382] | Meeeee, M. M.; Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [396] | Meeee, M.; Meee, M.; Meeeeeeeee, M.; Meeee, M., Meeee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
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