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Regioselective rhodium(I)-catalyzed hydroarylation of protected allylic amines with arylboronic acids.
Org Lett. 2010 Jun 04; 12(11):2456-9.OL

Abstract

A novel regioselective rhodium(I)-catalyzed hydroarylation of unactivated alkenes with arylboronic acids is described. The catalytic system employs [Rh(COD)OH](2) and BINAP to effect the addition of various arylboronic acids to protected allylic amines. The regioselectivity was found to be highly dependent on the protecting group, favoring the linear addition product with up to 92% yield and >20:1 regioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Tsui GC
Davenport Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5H 3H6.
Menard F
No affiliation info available
Lautens M
No affiliation info available

MeSH

Allyl CompoundsAminesBoronic AcidsCatalysisCombinatorial Chemistry TechniquesMolecular StructureRhodiumStereoisomerismStructure-Activity RelationshipTemperature

Pub Type(s)

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

Language

eng

PubMed ID

20455579

Citation

Tsui, Gavin Chit, et al. "Regioselective rhodium(I)-catalyzed Hydroarylation of Protected Allylic Amines With Arylboronic Acids." Organic Letters, vol. 12, no. 11, 2010, pp. 2456-9.
Tsui GC, Menard F, Lautens M. Regioselective rhodium(I)-catalyzed hydroarylation of protected allylic amines with arylboronic acids. Org Lett. 2010;12(11):2456-9.
Tsui, G. C., Menard, F., & Lautens, M. (2010). Regioselective rhodium(I)-catalyzed hydroarylation of protected allylic amines with arylboronic acids. Organic Letters, 12(11), 2456-9. https://doi.org/10.1021/ol100974f
Tsui GC, Menard F, Lautens M. Regioselective rhodium(I)-catalyzed Hydroarylation of Protected Allylic Amines With Arylboronic Acids. Org Lett. 2010 Jun 4;12(11):2456-9. PubMed PMID: 20455579.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Regioselective rhodium(I)-catalyzed hydroarylation of protected allylic amines with arylboronic acids. AU - Tsui,Gavin Chit, AU - Menard,Frederic, AU - Lautens,Mark, PY - 2010/5/12/entrez PY - 2010/5/12/pubmed PY - 2010/8/18/medline SP - 2456 EP - 9 JF - Organic letters JO - Org Lett VL - 12 IS - 11 N2 - A novel regioselective rhodium(I)-catalyzed hydroarylation of unactivated alkenes with arylboronic acids is described. The catalytic system employs [Rh(COD)OH](2) and BINAP to effect the addition of various arylboronic acids to protected allylic amines. The regioselectivity was found to be highly dependent on the protecting group, favoring the linear addition product with up to 92% yield and >20:1 regioselectivity. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20455579/Regioselective_rhodium_I__catalyzed_hydroarylation_of_protected_allylic_amines_with_arylboronic_acids_ L2 - https://doi.org/10.1021/ol100974f DB - PRIME DP - Unbound Medicine ER -