Tags

Type your tag names separated by a space and hit enter

Control of chemo-, regio-, and stereoselectivities in ligand-free Pd-catalyzed oxidative Heck reactions of arylboronic acids or alkenylboronate with allyl esters.
Org Lett. 2009 Jul 16; 11(14):2980-3.OL

Abstract

A ligand-free Pd-catalyzed highly selective oxidative Heck reaction of organoboronic acids with allyl esters was developed. Beta-H elimination is highly chemoselectively controlled, leading to gamma-substituted allyl esters, which is contrary to the traditional Heck-type reactions of allyl esters. Moreover, the regio- and stereoselectivities are also high due to the chelation between O and Pd atoms.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Su Y
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.
Jiao N
No affiliation info available

MeSH

Allyl CompoundsBoronic AcidsCatalysisEstersMolecular StructureOxidation-ReductionPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19534546

Citation

Su, Yijin, and Ning Jiao. "Control of Chemo-, Regio-, and Stereoselectivities in Ligand-free Pd-catalyzed Oxidative Heck Reactions of Arylboronic Acids or Alkenylboronate With Allyl Esters." Organic Letters, vol. 11, no. 14, 2009, pp. 2980-3.
Su Y, Jiao N. Control of chemo-, regio-, and stereoselectivities in ligand-free Pd-catalyzed oxidative Heck reactions of arylboronic acids or alkenylboronate with allyl esters. Org Lett. 2009;11(14):2980-3.
Su, Y., & Jiao, N. (2009). Control of chemo-, regio-, and stereoselectivities in ligand-free Pd-catalyzed oxidative Heck reactions of arylboronic acids or alkenylboronate with allyl esters. Organic Letters, 11(14), 2980-3. https://doi.org/10.1021/ol9009865
Su Y, Jiao N. Control of Chemo-, Regio-, and Stereoselectivities in Ligand-free Pd-catalyzed Oxidative Heck Reactions of Arylboronic Acids or Alkenylboronate With Allyl Esters. Org Lett. 2009 Jul 16;11(14):2980-3. PubMed PMID: 19534546.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Control of chemo-, regio-, and stereoselectivities in ligand-free Pd-catalyzed oxidative Heck reactions of arylboronic acids or alkenylboronate with allyl esters. AU - Su,Yijin, AU - Jiao,Ning, PY - 2009/6/19/entrez PY - 2009/6/19/pubmed PY - 2009/8/14/medline SP - 2980 EP - 3 JF - Organic letters JO - Org Lett VL - 11 IS - 14 N2 - A ligand-free Pd-catalyzed highly selective oxidative Heck reaction of organoboronic acids with allyl esters was developed. Beta-H elimination is highly chemoselectively controlled, leading to gamma-substituted allyl esters, which is contrary to the traditional Heck-type reactions of allyl esters. Moreover, the regio- and stereoselectivities are also high due to the chelation between O and Pd atoms. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19534546/Control_of_chemo__regio__and_stereoselectivities_in_ligand_free_Pd_catalyzed_oxidative_Heck_reactions_of_arylboronic_acids_or_alkenylboronate_with_allyl_esters_ L2 - https://doi.org/10.1021/ol9009865 DB - PRIME DP - Unbound Medicine ER -