One-pot sequential functionalizations of meso-tetrathienylporphyrins via Heck-Mizoroki cross-coupling reactions

Author(s)

Donatoni, Maria C. ^[1] ; Vieira, Ygor W. ^[1] ; Brocksom, Timothy J. ^[1] ; Rabelo, Adriano C. ^[1] ; Leite, Edson R. ^[1] ; de Oliveira, Kleber T. ^[1]

Affiliation

^[1] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: Tetrahedron Letters; v. 57, n. 27-28, p. 3016-3020, JUL 6 2016.
• Web of Science Citations: 4

Abstract

Synthesis and sequential functionalizations of a new meso-tetraiodo(thien-2-yl)porphyrin and its Ni(II) derivative are described. The reactions for the preparation of these new porphyrins were optimized. Subsequently, four successive one-pot Heck-Mizoroki cross-coupling reactions were studied using two acrylates and varied reaction conditions. We describe an optimized protocol for the preparation of highly conjugated thienylporphyrins with the potential to be used as dyes in solar cell devices as demonstrated in our preliminary studies. (C) 2016 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 11/13993-2 - Methodologies for the synthesis of bioactive terpenes
• Grantee: Timothy John Brocksom
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/07276-1 - CEPOF - Optics and Photonic Research Center
• Grantee: Vanderlei Salvador Bagnato
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 15/21110-4 - Exploiting Photocatalyzed Reactions Under Continuous Flow Conditions by using Porphyrinoid Systems: (C-FlowPhotoChem)
• Grantee: Kleber Thiago de Oliveira
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/06532-4 - Cross-coupling reactions on the synthesis of new photosensitizers with high conjugation
• Grantee: Kleber Thiago de Oliveira
• Support Opportunities: Regular Research Grants