Chemo-, Regio- and Stereoselective Heck Arylation of Allylated Malonates: Mechanistic Insights by ESI-MS and Synthetic Application toward 5-Arylmethyl-gamma-lactones

Author(s)

Oliveira, Caio C. ^[1] ; Marques, Marcelo V. ^[2] ; Godoi, Marla N. ^[3] ; Regiani, Thais ^[3] ; Santos, Vanessa G. ^[3] ; dos Santos, Emerson A. F. ^[1] ; Eberlin, Marcos N. ^[3] ; Sa, Marcus M. ^[2] ; Correia, Carlos R. D. ^[1]

Affiliation

^[1] Univ Estadual Campinas UNICAMP, Inst Quim, BR-13083970 Campinas, SP - Brazil

^[2] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC - Brazil

^[3] Univ Estadual Campinas UNICAMP, Lab ThoMSon Espectrometria Massas, BR-13083970 Campinas, SP - Brazil

• Document type: Journal article
• Source: ORGANIC LETTERS; v. 16, n. 19, p. 5180-5183, OCT 3 2014.
• Web of Science Citations: 16

Abstract

We descirbe herein a general method for the controlled Heck arylation of allylated malonates. Both electron-rich and electron poor aryldiazonium salts were readily employed as the aryl transfer agents in good yields and in high chemo-, regio-, and stereoselectivity without formation of decarboxylated byproducts. Reaction monitoring via ESI-MS was used to support the formation of chelated pd species through the catalytic cycle. Additionally, some Heck adducts were successfully used in the total synthesis of pharmacologically active gamma-lactones. (AU)

• FAPESP's process: 11/23832-6 - New methodological and mechanistic studies related to the Heck arylations employing arenediazonium salts and synthetic applications
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC