A Caltech Library Service

C–H bond functionalizations with palladium(II): intramolecular oxidative annulations of arenes

Ferreira, Eric M. and Zhang, Haiming and Stoltz, Brian M. (2008) C–H bond functionalizations with palladium(II): intramolecular oxidative annulations of arenes. Tetrahedron, 64 (26). pp. 5987-6001. ISSN 0040-4020. PMCID PMC2441596. doi:10.1016/j.tet.2008.01.052.

[img] PDF - Accepted Version
See Usage Policy.


Use this Persistent URL to link to this item:


Oxidative annulations for the synthesis of carbocycles were developed using a catalytic palladium(II) system. Indoles with pendant olefin tethers were oxidatively cyclized to form annulated products. Electron-rich aromatic systems were also investigated, culminating in the synthesis of benzofurans and dihydrobenzofurans by a similar protocol. These reactions were demonstrated to proceed by an initial C–H bond functionalization event, followed by olefin insertion and β-hydride elimination.

Item Type:Article
Related URLs:
URLURL TypeDescription CentralArticle
Zhang, Haiming0000-0002-2139-2598
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2008 Elsevier Ltd. Received 24 August 2007, Revised 13 October 2007, Accepted 15 October 2008, Available online 16 January 2008. The authors wish to thank the NIH-NIGMS (R01 GM65961-01), Bristol–Myers Squibb Company (graduate fellowship to E.M.F.), the NSF (graduate fellowship to E.M.F.), the Dreyfus Foundation, Merck Research Laboratories, Research Corporation, Abbott Laboratories, Pfizer, Amgen, GlaxoSmithKline, Lilly, Boehringer Ingelheim, and Johnson and Johnson for generous financial support.
Funding AgencyGrant Number
Bristol–Myers Squibb CompanyUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
Research CorporationUNSPECIFIED
Abbott LaboratoriesUNSPECIFIED
Johnson and JohnsonUNSPECIFIED
Issue or Number:26
PubMed Central ID:PMC2441596
Record Number:CaltechAUTHORS:20161128-075820774
Persistent URL:
Official Citation:Eric M. Ferreira, Haiming Zhang, Brian M. Stoltz, C–H bond functionalizations with palladium(II): intramolecular oxidative annulations of arenes, Tetrahedron, Volume 64, Issue 26, 23 June 2008, Pages 5987-6001, ISSN 0040-4020, (
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:72290
Deposited By: Ruth Sustaita
Deposited On:28 Nov 2016 19:41
Last Modified:11 Nov 2021 04:59

Repository Staff Only: item control page