Synthesis of brominated directly fused diporphyrins through gold(III)-mediated oxidation

Akhila K Sahoo; Yasuyuki Nakamura; Naoki Aratani; Kil Suk Kim; Su Bum Noh; Hiroshi Shinokubo; Dongho Kim; Atsuhiro Osuka

doi:10.1021/ol061763f

Synthesis of brominated directly fused diporphyrins through gold(III)-mediated oxidation

Org Lett. 2006 Aug 31;8(18):4141-4. doi: 10.1021/ol061763f.

Authors

Akhila K Sahoo¹, Yasuyuki Nakamura, Naoki Aratani, Kil Suk Kim, Su Bum Noh, Hiroshi Shinokubo, Dongho Kim, Atsuhiro Osuka

Affiliation

¹ Department of Chemistry, Graduate School of Science, Kyoto University and CREST, Japan Science and Technology Agency (JST), Kyoto University, Kyoto 606-8502, Japan.

PMID: 16928094
DOI: 10.1021/ol061763f

Abstract

Highly efficient synthesis of meso,meso-dibromo doubly and triply fused diporphyrins has been achieved through a powerful oxidative coupling mediated by AuCl3-AgOTf combination. In addition, palladium-catalyzed debromination of meso-bromoporphyrins has been developed. This debromination protocol enables employment of bromine as a protecting group for the reactive meso-position of porphyrins.

Publication types

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

MeSH terms

Bromine / chemistry
Gold / chemistry*
Molecular Structure
Oxidation-Reduction
Porphyrins / chemical synthesis*

Substances

Porphyrins
Gold
Bromine