Sulfur-assisted interconversion between N-confused porphyrin and N-fused porphyrin

Satoshi Touden, Yoshiya Ikawa, Ryuichi Sakashita, Motoki Toganoh, Shigeki Mori, Hiroyuki Furuta

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The ring-opening reaction of N-fused tetraphenylporphyrin (NFTPP-H, 2) to C3-substituted N-confused tetraphenylporphyrin (NCTPP-S-Ar, 4) proceeded efficiently in 85-95% yields. Furthermore, removal of the C3-arylthio- substituents in 4 was achieved by the two types of desulfurization reactions. The Ni 2B-mediated desulfurization afforded C3-free N-confused tetraphenylporphyrin (NCTPP-H, 1) whereas the radical-mediated desulfurization with (n-Bu) 3Sn-H and AIBN promoted the ring-fusion to afford 2.

Original languageEnglish
Pages (from-to)6071-6074
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number45
DOIs
Publication statusPublished - Nov 7 2012

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Porphyrins
Desulfurization
Sulfur
Fusion reactions
tetraphenylporphyrin

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Sulfur-assisted interconversion between N-confused porphyrin and N-fused porphyrin. / Touden, Satoshi; Ikawa, Yoshiya; Sakashita, Ryuichi; Toganoh, Motoki; Mori, Shigeki; Furuta, Hiroyuki.

In: Tetrahedron Letters, Vol. 53, No. 45, 07.11.2012, p. 6071-6074.

Research output: Contribution to journalArticle

Touden, Satoshi ; Ikawa, Yoshiya ; Sakashita, Ryuichi ; Toganoh, Motoki ; Mori, Shigeki ; Furuta, Hiroyuki. / Sulfur-assisted interconversion between N-confused porphyrin and N-fused porphyrin. In: Tetrahedron Letters. 2012 ; Vol. 53, No. 45. pp. 6071-6074.
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