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Silver-catalyzed regioselective carbomagnesiation of alkynes with alkyl halides and Grignard reagents.
Org Lett. 2011 Sep 02; 13(17):4656-9.OL

Abstract

A silver-catalyzed carbomagnesiation of alkynes with alkyl halides and Grignard reagents afforded alkenyl Grignard reagents regioselectively, where the alkyl group of the alkyl halide, but not that of the Grignard reagent, was introduced into the alkyne. Application to δ-haloalkylacetylenes yielded cyclopentanes or a tetrahydrofuran containing an exo-methylene substituent via 5-exo-dig cyclization.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Kambe N
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 Japan. kambe@chem.eng.osaka-u.ac.jp
Moriwaki Y
No affiliation info available
Fujii Y
No affiliation info available
Iwasaki T
No affiliation info available
Terao J
No affiliation info available

MeSH

AlkynesCatalysisCyclizationCyclopentanesFuransHydrocarbons, HalogenatedMolecular StructureOrganometallic CompoundsSilverStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21806040

Citation

Kambe, Nobuaki, et al. "Silver-catalyzed Regioselective Carbomagnesiation of Alkynes With Alkyl Halides and Grignard Reagents." Organic Letters, vol. 13, no. 17, 2011, pp. 4656-9.
Kambe N, Moriwaki Y, Fujii Y, et al. Silver-catalyzed regioselective carbomagnesiation of alkynes with alkyl halides and Grignard reagents. Org Lett. 2011;13(17):4656-9.
Kambe, N., Moriwaki, Y., Fujii, Y., Iwasaki, T., & Terao, J. (2011). Silver-catalyzed regioselective carbomagnesiation of alkynes with alkyl halides and Grignard reagents. Organic Letters, 13(17), 4656-9. https://doi.org/10.1021/ol2018664
Kambe N, et al. Silver-catalyzed Regioselective Carbomagnesiation of Alkynes With Alkyl Halides and Grignard Reagents. Org Lett. 2011 Sep 2;13(17):4656-9. PubMed PMID: 21806040.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Silver-catalyzed regioselective carbomagnesiation of alkynes with alkyl halides and Grignard reagents. AU - Kambe,Nobuaki, AU - Moriwaki,Yuusuke, AU - Fujii,Yuuki, AU - Iwasaki,Takanori, AU - Terao,Jun, Y1 - 2011/08/01/ PY - 2011/8/3/entrez PY - 2011/8/3/pubmed PY - 2011/12/13/medline SP - 4656 EP - 9 JF - Organic letters JO - Org Lett VL - 13 IS - 17 N2 - A silver-catalyzed carbomagnesiation of alkynes with alkyl halides and Grignard reagents afforded alkenyl Grignard reagents regioselectively, where the alkyl group of the alkyl halide, but not that of the Grignard reagent, was introduced into the alkyne. Application to δ-haloalkylacetylenes yielded cyclopentanes or a tetrahydrofuran containing an exo-methylene substituent via 5-exo-dig cyclization. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21806040/Silver_catalyzed_regioselective_carbomagnesiation_of_alkynes_with_alkyl_halides_and_Grignard_reagents_ L2 - https://doi.org/10.1021/ol2018664 DB - PRIME DP - Unbound Medicine ER -