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Please login or sign up for a free trial to access the full content.2.11.8.8.1 Variation 1: Using Grignard or Other Magnesium Reagents
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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 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee Meeeeeeeee Meeeee[888]
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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 Y-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]
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Meeeee 888 Meeeeeeee(MM)-Meeeeeeee Meeeeeeeeeeeeee[888–888]
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Meeeee 888 Meeeeeeee(MM)-Meeeeeeee Meeeeeeeeee Meeeeeeee[888]
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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]
e Meeee 88 eee% (M)-88 eee MeMeMe (8 eeeee).
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References
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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