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

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

doi:10.1016/j.tetlet.2012.08.131

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 journal › Article › peer-review

13 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 language	English
Pages (from-to)	6071-6074
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	45
DOIs	https://doi.org/10.1016/j.tetlet.2012.08.131
Publication status	Published - Nov 7 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.08.131

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@article{52252e9061e14274a2af8b43e993a56e,

title = "Sulfur-assisted interconversion between N-confused porphyrin and N-fused porphyrin",

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.",

author = "Satoshi Touden and Yoshiya Ikawa and Ryuichi Sakashita and Motoki Toganoh and Shigeki Mori and Hiroyuki Furuta",

note = "Funding Information: This work is supported by Grants-in-Aids for Challenging Exploratory Research (No. 23655159 to Y.I.), on Innovative Areas “ Emergence in Chemistry ” (No. 21111518 to Y.I.) and “ Emergence of highly elaborated π-space and its function ” (No. 21108518 to H.F.) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan. ",

year = "2012",

month = nov,

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doi = "10.1016/j.tetlet.2012.08.131",

language = "English",

volume = "53",

pages = "6071--6074",

journal = "Tetrahedron Letters",

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T1 - Sulfur-assisted interconversion between N-confused porphyrin and N-fused porphyrin

AU - Touden, Satoshi

AU - Ikawa, Yoshiya

AU - Sakashita, Ryuichi

AU - Toganoh, Motoki

AU - Mori, Shigeki

AU - Furuta, Hiroyuki

N1 - Funding Information: This work is supported by Grants-in-Aids for Challenging Exploratory Research (No. 23655159 to Y.I.), on Innovative Areas “ Emergence in Chemistry ” (No. 21111518 to Y.I.) and “ Emergence of highly elaborated π-space and its function ” (No. 21108518 to H.F.) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan.

PY - 2012/11/7

Y1 - 2012/11/7

N2 - 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.

AB - 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.

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M3 - Article

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EP - 6074

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

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

Abstract

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