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Titanocene-catalyzed regioselective alkylation of styrenes with grignard reagents using beta-bromoethyl ethers, thioethers, or amines.
Chem Asian J. 2008 Sep 01; 3(8-9):1472-8.CA

Abstract

Regioselective double alkylation of styrenes with alkyl Grignard reagents and alkyl bromides having a heteroatom functional group at the beta-position has been achieved by the use of a titanocene catalyst in THF. When ether was used instead of THF as a solvent, monoalkylation by substitution of a vinylic hydrogen atom with an alkyl group proceeded under similar conditions. These reactions involve the addition of alkyl radicals to styrenes to form benzylic radical intermediates.

Authors+Show Affiliations

Science and Technology Centre for Atoms, Molecules and Ions Control, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan. terao@chem.eng.osaka-u.ac.jpNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18613206

Citation

Terao, Jun, et al. "Titanocene-catalyzed Regioselective Alkylation of Styrenes With Grignard Reagents Using Beta-bromoethyl Ethers, Thioethers, or Amines." Chemistry, an Asian Journal, vol. 3, no. 8-9, 2008, pp. 1472-8.
Terao J, Kato Y, Kambe N. Titanocene-catalyzed regioselective alkylation of styrenes with grignard reagents using beta-bromoethyl ethers, thioethers, or amines. Chem Asian J. 2008;3(8-9):1472-8.
Terao, J., Kato, Y., & Kambe, N. (2008). Titanocene-catalyzed regioselective alkylation of styrenes with grignard reagents using beta-bromoethyl ethers, thioethers, or amines. Chemistry, an Asian Journal, 3(8-9), 1472-8. https://doi.org/10.1002/asia.200800134
Terao J, Kato Y, Kambe N. Titanocene-catalyzed Regioselective Alkylation of Styrenes With Grignard Reagents Using Beta-bromoethyl Ethers, Thioethers, or Amines. Chem Asian J. 2008 Sep 1;3(8-9):1472-8. PubMed PMID: 18613206.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Titanocene-catalyzed regioselective alkylation of styrenes with grignard reagents using beta-bromoethyl ethers, thioethers, or amines. AU - Terao,Jun, AU - Kato,Yuichiro, AU - Kambe,Nobuaki, PY - 2008/7/10/pubmed PY - 2008/7/10/medline PY - 2008/7/10/entrez SP - 1472 EP - 8 JF - Chemistry, an Asian journal JO - Chem Asian J VL - 3 IS - 8-9 N2 - Regioselective double alkylation of styrenes with alkyl Grignard reagents and alkyl bromides having a heteroatom functional group at the beta-position has been achieved by the use of a titanocene catalyst in THF. When ether was used instead of THF as a solvent, monoalkylation by substitution of a vinylic hydrogen atom with an alkyl group proceeded under similar conditions. These reactions involve the addition of alkyl radicals to styrenes to form benzylic radical intermediates. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/18613206/Titanocene_catalyzed_regioselective_alkylation_of_styrenes_with_grignard_reagents_using_beta_bromoethyl_ethers_thioethers_or_amines_ L2 - https://doi.org/10.1002/asia.200800134 DB - PRIME DP - Unbound Medicine ER -
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