Synthesis of substituted benzoxacycles via a domino ortho-alkylation/Heck coupling sequence

Andrew Martins; Udo Marquardt; Neema Kasravi; Dino Alberico; Mark Lautens

doi:10.1021/jo060552l

Synthesis of substituted benzoxacycles via a domino ortho-alkylation/Heck coupling sequence

J Org Chem. 2006 Jun 23;71(13):4937-42. doi: 10.1021/jo060552l.

Authors

Andrew Martins¹, Udo Marquardt, Neema Kasravi, Dino Alberico, Mark Lautens

Affiliation

¹ Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada.

PMID: 16776524
DOI: 10.1021/jo060552l

Abstract

The synthesis of a variety of alkylidene benzoxacycles via a domino palladium-catalyzed ortho-alkylation/intramolecular Heck reaction is described. Under the optimized conditions [Pd(OAc)2 (10 mol %), P(2-Furyl)3 (20 mol %), norbornene (4 equiv), Cs2CO3 (2 equiv), CH3CN, 80 degrees C], aryl iodides with oxygen-tethered Heck acceptors are coupled with alkyl bromides (5 equiv) to generate a variety of six- and seven-membered-ring benzoxacyclic products.

Publication types

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

MeSH terms

Alkylation
Benzoxazines / chemical synthesis*
Benzoxazines / chemistry
Catalysis
Cyclization
Molecular Structure
Palladium / chemistry
Stereoisomerism

Substances

Benzoxazines
Palladium