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Sulfur-assisted interconversion between N-confused porphyrin and N-fused porphyrin |
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| Authors: | Satoshi ToudenYoshiya Ikawa Ryuichi SakashitaMotoki Toganoh Shigeki MoriHiroyuki Furuta |
| Affiliation: | a Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan b International Research Center for Molecular Systems (IRCMS), Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan c Department of Molecular Science, Integrated Center for Sciences, Ehime University, 2-5 Bunkyo-cho, Matsuyama 790-8577, Japan |
| 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 Ni2B-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. |
| Keywords: | N-confused porphyrin N-fused porphyrin Sulfur nucleophile Reductive desulfurization |
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