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Diversity-oriented synthesis of multisubstituted olefins through the sequential integration of palladium-catalyzed cross-coupling reactions. 2-pyridyldimethyl(vinyl)silane as a versatile platform for olefin synthesis.
J Am Chem Soc 2001; 123(47):11577-85JA

Abstract

A novel strategy for the diversity-oriented synthesis of multisubstituted olefins, where 2-pyridyldimethyl(vinyl)silane functions as a versatile platform for olefin synthesis, is described. The palladium-catalyzed Heck-type coupling of 2-pyridyldimethyl(vinyl)silanes with organic iodides took place in the presence of Pd2(dba)3/tri-2-furylphosphine catalyst to give beta-substituted vinylsilanes in excellent yields. The Heck-type coupling occurred even with alpha- and beta-substituted 2-pyridyldimethyl(vinyl)silanes. The one-pot double Heck coupling of 2-pyridyldimethyl(vinyl)silane took place with two different aryl iodides to afford beta,beta-diarylated vinylsilanes in good yields. The palladium-catalyzed Hiyama-type coupling of 2-pyridyldimethyl(vinyl)silane with organic halides took place in the presence of tetrabutylammonium fluoride to give di- and trisubstituted olefins in high yields. The sequential integration of Heck-type (or double Heck) coupling and Hiyama-type coupling produced the multisubstituted olefins in regioselective, stereoselective, and diversity-oriented fashions. Especially, the one-pot sequential Heck/Hiyama coupling reaction provides an extremely facile entry into a diverse range of stereodefined multisubstituted olefins. Mechanistic considerations of both Heck-type and Hiyama-type coupling reactions are also described.

Authors+Show Affiliations

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

11716711

Citation

Itami, K, et al. "Diversity-oriented Synthesis of Multisubstituted Olefins Through the Sequential Integration of Palladium-catalyzed Cross-coupling Reactions. 2-pyridyldimethyl(vinyl)silane as a Versatile Platform for Olefin Synthesis." Journal of the American Chemical Society, vol. 123, no. 47, 2001, pp. 11577-85.
Itami K, Nokami T, Ishimura Y, et al. Diversity-oriented synthesis of multisubstituted olefins through the sequential integration of palladium-catalyzed cross-coupling reactions. 2-pyridyldimethyl(vinyl)silane as a versatile platform for olefin synthesis. J Am Chem Soc. 2001;123(47):11577-85.
Itami, K., Nokami, T., Ishimura, Y., Mitsudo, K., Kamei, T., & Yoshida, J. (2001). Diversity-oriented synthesis of multisubstituted olefins through the sequential integration of palladium-catalyzed cross-coupling reactions. 2-pyridyldimethyl(vinyl)silane as a versatile platform for olefin synthesis. Journal of the American Chemical Society, 123(47), pp. 11577-85.
Itami K, et al. Diversity-oriented Synthesis of Multisubstituted Olefins Through the Sequential Integration of Palladium-catalyzed Cross-coupling Reactions. 2-pyridyldimethyl(vinyl)silane as a Versatile Platform for Olefin Synthesis. J Am Chem Soc. 2001 Nov 28;123(47):11577-85. PubMed PMID: 11716711.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Diversity-oriented synthesis of multisubstituted olefins through the sequential integration of palladium-catalyzed cross-coupling reactions. 2-pyridyldimethyl(vinyl)silane as a versatile platform for olefin synthesis. AU - Itami,K, AU - Nokami,T, AU - Ishimura,Y, AU - Mitsudo,K, AU - Kamei,T, AU - Yoshida,J, PY - 2001/11/22/pubmed PY - 2002/2/6/medline PY - 2001/11/22/entrez SP - 11577 EP - 85 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 123 IS - 47 N2 - A novel strategy for the diversity-oriented synthesis of multisubstituted olefins, where 2-pyridyldimethyl(vinyl)silane functions as a versatile platform for olefin synthesis, is described. The palladium-catalyzed Heck-type coupling of 2-pyridyldimethyl(vinyl)silanes with organic iodides took place in the presence of Pd2(dba)3/tri-2-furylphosphine catalyst to give beta-substituted vinylsilanes in excellent yields. The Heck-type coupling occurred even with alpha- and beta-substituted 2-pyridyldimethyl(vinyl)silanes. The one-pot double Heck coupling of 2-pyridyldimethyl(vinyl)silane took place with two different aryl iodides to afford beta,beta-diarylated vinylsilanes in good yields. The palladium-catalyzed Hiyama-type coupling of 2-pyridyldimethyl(vinyl)silane with organic halides took place in the presence of tetrabutylammonium fluoride to give di- and trisubstituted olefins in high yields. The sequential integration of Heck-type (or double Heck) coupling and Hiyama-type coupling produced the multisubstituted olefins in regioselective, stereoselective, and diversity-oriented fashions. Especially, the one-pot sequential Heck/Hiyama coupling reaction provides an extremely facile entry into a diverse range of stereodefined multisubstituted olefins. Mechanistic considerations of both Heck-type and Hiyama-type coupling reactions are also described. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/11716711/Diversity_oriented_synthesis_of_multisubstituted_olefins_through_the_sequential_integration_of_palladium_catalyzed_cross_coupling_reactions__2_pyridyldimethyl_vinyl_silane_as_a_versatile_platform_for_olefin_synthesis_ L2 - https://dx.doi.org/10.1021/ja016790+ DB - PRIME DP - Unbound Medicine ER -