- Co-catalyzed cross-coupling of alkyl halides with tertiary alkyl Grignard reagents using a 1,3-butadiene additive
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The cobalt-catalyzed cross-coupling of alkyl (pseudo)halides with alkyl Grignard reagents in the presence of 1,3-butadiene as a ligand precursor and LiI is described. Sterically congested quaternary carbon centers could be constructed by using tertiary alkyl Grignard reagents. This reaction proceeds via an ionic mechanism with inversion of stereochemistry at the reacting site of the alkyl halide and is compatible with various functional groups. The use of both 1,3-butadiene and LiI was essential for achieving high yields and high selectivities.
- Iwasaki, Takanori,Takagawa, Hiroaki,Singh, Surya P.,Kuniyasu, Hitoshi,Kambe, Nobuaki
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supporting information
p. 9604 - 9607
(2013/07/26)
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- New syntheses of 1,7-dimethylnonyl propanoate, the western corn rootworm pheromone, in four different ways via cross metathesis, alkylation and coupling reactionsss
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A mixture of the four stereoisomers of 1,7-dimethylnonyl propanoate, the female sex pheromone of the western corn rootworm (Diabrotica virgifera virgifera LeConte), was synthesized in four different ways by employing one of the following four reactions as the key step: (i) cross metathesis using the Grubbs I catalyst, (ii) cross metathesis using the Grubbs II catalyst, (iii) alkylation of an alkynide anion, and (iv) Grignard coupling in the presence of dilithium tetrachlorocuprate. Although the cross metathesis approaches enabled two short syntheses (4 or 6 steps) of the pheromone to be achieved, the cheapest and most efficient synthesis was possible via Grignard coupling to give the desired pheromone in a 40% overall yield based on 2-methyl-1-butanol (8 steps).
- Mori, Kenji
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p. 595 - 600
(2011/04/23)
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- Pd-Catalyzed Cross-Coupling Reaction of Alkyl Tosylates and Bromides with Grignard Reagents in the Presence of 1,3-Butadiene
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A new method for cross-coupling reaction of alkyl tosylates and bromides with Grignard reagents has been developed by the use of Pd(acac)2 or PdCl2 as the catalyst. Addition of 1,3-butadiene is essential to afford good yields of coupling products. This reaction proceeds efficiently at room temperature using primary and secondary alkyl and aryl Grignard reagents.
- Terao, Jun,Naitoh, Yoshitaka,Kuniyasu, Hitoshi,Kambe, Nobuaki
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p. 890 - 891
(2007/10/03)
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- Identification of the Aggregation Pheromone of Flour Beetles Tribolium castaneum and T. confusum (Coleoptera: Tenebrionidae)
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The aggregation pheromone produced by the male red flour beetle Tribolium castaneum, and confused flour beetles, T. confusum was identified as 4,8-dimethyldecan-1-al by GLC, GC-MS, PMR spectra, and synthesis of the compound.The synthetic pheromone was less attractive compared with the natural pheromone, because the synthetic sample was composed of four optical isomers.
- Suzuki, Takahisa
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p. 1357 - 1364
(2007/10/02)
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