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Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative Heck reactions.
J Am Chem Soc 2012; 134(40):16496-9JA

Abstract

Pd-catalyzed aerobic oxidative coupling of vinylboronic acids and electronically unbiased alkyl olefins provides regioselective access to 1,3-disubstituted conjugated dienes. Catalyst-controlled regioselectivity is achieved by using 2,9-dimethylphenanthroline as a ligand. The observed regioselectivity is opposite to that observed from a traditional (nonoxidative) Heck reaction between a vinyl bromide and an alkene. DFT computational studies reveal that steric effects of the 2,9-dimethylphenanthroline ligand promote C-C bond formation at the internal position of the alkene.

Authors+Show Affiliations

Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

22998540

Citation

Zheng, Changwu, et al. "Catalyst-controlled Regioselectivity in the Synthesis of Branched Conjugated Dienes Via Aerobic Oxidative Heck Reactions." Journal of the American Chemical Society, vol. 134, no. 40, 2012, pp. 16496-9.
Zheng C, Wang D, Stahl SS. Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative Heck reactions. J Am Chem Soc. 2012;134(40):16496-9.
Zheng, C., Wang, D., & Stahl, S. S. (2012). Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative Heck reactions. Journal of the American Chemical Society, 134(40), pp. 16496-9. doi:10.1021/ja307371w.
Zheng C, Wang D, Stahl SS. Catalyst-controlled Regioselectivity in the Synthesis of Branched Conjugated Dienes Via Aerobic Oxidative Heck Reactions. J Am Chem Soc. 2012 Oct 10;134(40):16496-9. PubMed PMID: 22998540.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative Heck reactions. AU - Zheng,Changwu, AU - Wang,Dian, AU - Stahl,Shannon S, Y1 - 2012/09/28/ PY - 2012/9/25/entrez PY - 2012/9/25/pubmed PY - 2013/3/2/medline SP - 16496 EP - 9 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 134 IS - 40 N2 - Pd-catalyzed aerobic oxidative coupling of vinylboronic acids and electronically unbiased alkyl olefins provides regioselective access to 1,3-disubstituted conjugated dienes. Catalyst-controlled regioselectivity is achieved by using 2,9-dimethylphenanthroline as a ligand. The observed regioselectivity is opposite to that observed from a traditional (nonoxidative) Heck reaction between a vinyl bromide and an alkene. DFT computational studies reveal that steric effects of the 2,9-dimethylphenanthroline ligand promote C-C bond formation at the internal position of the alkene. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/22998540/Catalyst_controlled_regioselectivity_in_the_synthesis_of_branched_conjugated_dienes_via_aerobic_oxidative_Heck_reactions_ L2 - https://dx.doi.org/10.1021/ja307371w DB - PRIME DP - Unbound Medicine ER -