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

Research output: Contribution to journalArticle

68 Citations (Scopus)

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 mesobromoporphyrins has been developed. This debromination protocol enables employment of bromine as a protecting group for the reactive meso-position of porphyrins.

Original languageEnglish
Pages (from-to)4141-4144
Number of pages4
JournalOrganic Letters
Volume8
Issue number18
DOIs
Publication statusPublished - 2006 Aug 31

Fingerprint

Oxidative Coupling
Bromine
Porphyrins
Palladium
bromine
porphyrins
Gold
palladium
gold
Oxidation
oxidation
synthesis

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Sahoo, A. K., Nakamura, Y., Aratani, N., Kim, K. S., Noh, S. B., Shinokubo, H., ... Osuka, A. (2006). Synthesis of brominated directly fused diporphyrins through gold(III)-mediated oxidation. Organic Letters, 8(18), 4141-4144. https://doi.org/10.1021/ol061763f
Sahoo, Akhila K. ; Nakamura, Yasuyuki ; Aratani, Naoki ; Kim, Kil Suk ; Noh, Su Bum ; Shinokubo, Hiroshi ; Kim, Dongho ; Osuka, Atsuhiro. / Synthesis of brominated directly fused diporphyrins through gold(III)-mediated oxidation. In: Organic Letters. 2006 ; Vol. 8, No. 18. pp. 4141-4144.
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Sahoo, AK, Nakamura, Y, Aratani, N, Kim, KS, Noh, SB, Shinokubo, H, Kim, D & Osuka, A 2006, 'Synthesis of brominated directly fused diporphyrins through gold(III)-mediated oxidation', Organic Letters, vol. 8, no. 18, pp. 4141-4144. https://doi.org/10.1021/ol061763f

Synthesis of brominated directly fused diporphyrins through gold(III)-mediated oxidation. / Sahoo, Akhila K.; Nakamura, Yasuyuki; Aratani, Naoki; Kim, Kil Suk; Noh, Su Bum; Shinokubo, Hiroshi; Kim, Dongho; Osuka, Atsuhiro.

In: Organic Letters, Vol. 8, No. 18, 31.08.2006, p. 4141-4144.

Research output: Contribution to journalArticle

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AU - Noh, Su Bum

AU - Shinokubo, Hiroshi

AU - Kim, Dongho

AU - Osuka, Atsuhiro

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Sahoo AK, Nakamura Y, Aratani N, Kim KS, Noh SB, Shinokubo H et al. Synthesis of brominated directly fused diporphyrins through gold(III)-mediated oxidation. Organic Letters. 2006 Aug 31;8(18):4141-4144. https://doi.org/10.1021/ol061763f