Atsuhiro Osuka

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5,18‐Dimesitylorangarin: a Stable Antiaromatic [20]Pentaphyrin(1.0.1.0.0) Displaying Remarkable Oxidative Self‐Coupling Reactions

Yutao Rao, Jiyeon Lee, Jinchao Chen, Ling Xu, more

Angewandte Chemie International Edition > 63 > 38 > n/a - n/a

5,18‐Dimesitylorangarin and its BF₂ complex were synthesized by double S_NAr reaction of 3,5‐dibromo‐BODIPY with 2‐pyrrolydipyrrin as the first examples of meso‐aryl‐substituted orangarin. These orangarins, delineated as [20]pentaphyrin(1.0.1.0.0), are strongly antiaromatic but rather stable. The free base orangarin was coupled by oxidation with MnO₂ to give a 11,11′‐linked dimer, a cyclooctatetraene(COT)‐centered...

article

5,18‐Dimesitylorangarin: a Stable Antiaromatic [20]Pentaphyrin(1.0.1.0.0) Displaying Remarkable Oxidative Self‐Coupling Reactions

Yutao Rao, Jiyeon Lee, Jinchao Chen, Ling Xu, more

Angewandte Chemie > 136 > 38 > n/a - n/a

5,18‐Dimesitylorangarin and its BF₂ complex were synthesized by double S_NAr reaction of 3,5‐dibromo‐BODIPY with 2‐pyrrolydipyrrin as the first examples of meso‐aryl‐substituted orangarin. These orangarins, delineated as [20]pentaphyrin(1.0.1.0.0), are strongly antiaromatic but rather stable. The free base orangarin was coupled by oxidation with MnO₂ to give a 11,11′‐linked dimer, a cyclooctatetraene(COT)‐centered...

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[22]Pentaphyrins(2.0.1.1.0) Displaying N‐Fusion, Pyrrole‐Rearrangement, and Dimerization Reactions Upon Oxidation and Metalation

Jinchao Chen, Le Liu, Yutao Rao, Ling Xu, more

Angewandte Chemie International Edition > 63 > 34 > n/a - n/a

Exploration of expanded porphyrins with unprecedented reactivities has remained important. Here [22]pentaphyrins(2.0.1.1.0) were synthesized as a constitutional isomer of sapphyrin by acid‐catalyzed cyclization of 1,14‐dibromo‐5,10‐diaryltripyrrin with 1,2‐di(pyrro‐2‐ly)ethenes. These pentaphyrins display roughly planar structures and varying aromaticities depending upon the vinylene structures. The...

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[22]Pentaphyrins(2.0.1.1.0) Displaying N‐Fusion, Pyrrole‐Rearrangement, and Dimerization Reactions Upon Oxidation and Metalation

Jinchao Chen, Le Liu, Yutao Rao, Ling Xu, more

Angewandte Chemie > 136 > 34 > n/a - n/a

Exploration of expanded porphyrins with unprecedented reactivities has remained important. Here [22]pentaphyrins(2.0.1.1.0) were synthesized as a constitutional isomer of sapphyrin by acid‐catalyzed cyclization of 1,14‐dibromo‐5,10‐diaryltripyrrin with 1,2‐di(pyrro‐2‐ly)ethenes. These pentaphyrins display roughly planar structures and varying aromaticities depending upon the vinylene structures. The...

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A Triply Linked Porphyrin‐Norcorrole Hybrid with Singlet Diradical Character

Kaisheng Wang, Satoru Ito, Shuang Ren, Daiki Shimizu, more

Angewandte Chemie International Edition > 63 > 16 > n/a - n/a

Norcorrole Ni(II) complexes have recently received considerable attention because they are readily accessible antiaromatic molecules. Their high stability under ambient conditions and ease of synthesis have enabled the exploration of the intrinsic properties of antiaromatic molecules. Here, we report the synthesis and properties of meso–meso singly linked porphyrin‐norcorrole hybrids and a triply...

article

A Triply Linked Porphyrin‐Norcorrole Hybrid with Singlet Diradical Character

Kaisheng Wang, Satoru Ito, Shuang Ren, Daiki Shimizu, more

Angewandte Chemie > 136 > 16 > n/a - n/a

Norcorrole Ni(II) complexes have recently received considerable attention because they are readily accessible antiaromatic molecules. Their high stability under ambient conditions and ease of synthesis have enabled the exploration of the intrinsic properties of antiaromatic molecules. Here, we report the synthesis and properties of meso–meso singly linked porphyrin‐norcorrole hybrids and a triply...

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Synthesis of Pyrrole‐Sharing Fused Porphyrinoid Hybrids by Post‐fabrication of Ni(II) Porphyrins

Lili Zi, Li Liu, Mingbo Zhou, Le Liu, more

Angewandte Chemie International Edition > 63 > 8 > n/a - n/a

Pyrrole‐sharing fused hybrids of Ni^II porphyrin with Pd^II N‐confused(NC)‐corrole and Pd^II NC‐oxaporphyrin were synthesized by post‐fabrication of Ni^II porphyrins. Specifically this consists of Friedel–Crafts type aromatic substitution reaction of meso‐free Ni^II porphyrin with α,α′‐dibromotripyrrin and Pd(OAc)₂ assisted cyclization, and final heating to induce a Pd−C bond formation. Ni^II porphyrins...

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Synthesis of Pyrrole‐Sharing Fused Porphyrinoid Hybrids by Post‐fabrication of Ni(II) Porphyrins

Lili Zi, Li Liu, Mingbo Zhou, Le Liu, more

Angewandte Chemie > 136 > 8 > n/a - n/a

Pyrrole‐sharing fused hybrids of Ni^II porphyrin with Pd^II N‐confused(NC)‐corrole and Pd^II NC‐oxaporphyrin were synthesized by post‐fabrication of Ni^II porphyrins. Specifically this consists of Friedel–Crafts type aromatic substitution reaction of meso‐free Ni^II porphyrin with α,α′‐dibromotripyrrin and Pd(OAc)₂ assisted cyclization, and final heating to induce a Pd−C bond formation. Ni^II porphyrins...

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Cyclic Azobenzene‐BODIPY Hybrids

Bin Wen, Chao Li, Byeongjoo Kang, Tao Zheng, more

Chemistry – A European Journal > 30 > 6 > n/a - n/a

Cyclic azobenzene‐BODIPY hybrids were synthesized via cyclization by 1) acid‐catalysed condensation of azobenzene‐bridged dipyrroles with 3,5‐di‐tert‐butylbenzaldehyde, 2) oxidation with DDQ, and 3) metalation with BF₃ ⋅ Et₂O. The structures of many cyclic hybrids have been confirmed by single crystal X‐ray analysis. The absorption spectra of the hybrids reveal the effective cyclic conjugation. The...

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Gated Photochromism of Dithienylethene‐Embedded Expanded Calixphyrins

Fenni Zhang, Yutao Rao, Mingbo Zhou, Ling Xu, more

Chemistry – A European Journal > 29 > 62 > n/a - n/a

Dithienylethene (DTE)‐embedded expanded porphyrins were synthesized and confirmed to be photochemically inactive due to the lowest excited state of the expanded porphyrins. On the other hand, DTE‐embedded expanded calixphyrins exhibited reversible photochromism upon UV‐irradiation to form colored closed forms, which reverted to colorless open forms upon red‐light irradiation. The closed forms were...

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Post‐Installation of Fused Benzoheptagons at the Periphery of NiII Porphyrins: Helical Structures and Conformation‐Adjustable Fullerenes Binding

Kaisheng Wang, Yutao Rao, Ling Xu, Mingbo Zhou, more

Chemistry – A European Journal > 29 > 59 > n/a - n/a

Fused‐benzoheptagon‐installed Ni^II porphyrins were synthesized by a protocol consisting of (2‐formyl)arylation at the meso‐position(s) of Ni^II porphyrins, conversion of formyl group to methoxyethene group by Wittig reaction, and final Bi(OTf)₃‐catalyzed cyclization. The structures of these porphyrins have been revealed by X‐ray analysis. Owing to the installed heptagon ring(s), these porphyrins show...

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Oxidation of 3‐Oxo‐N‐Confused Porphyrin with PIFA: Inner and meso Functionalizations

Yihuan Zhang, Haoran Liu, Huowang He, Bo Zou, more

European Journal of Organic Chemistry > 26 > 35 > n/a - n/a

Conjugate addition of ethanol and subsequent oxidation with [bis (trifluoroacetoxy)iodo]benzene (PIFA) allowed for the inner ethoxylation of 3‐oxo‐N‐confused tetraphenylporphyrin (ONCP). First oxidation of ONCP with PIFA followed by treatment with ethanol gave two more N‐confused phlorins derivatives 5 and 6.

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A Quadruply Bridged Non‐Offset Face‐to‐Face Porphyrin Dimer and Cross‐Shaped Pentameric Porphyrin Tapes Based on 2,7,12,17‐Tetrakis(pinacolatoboryl) Ni^II Porphyrin

Meng Ye, Fangling Deng, Ling Xu, Yutao Rao, more

Angewandte Chemie International Edition > 62 > 13 > n/a - n/a

2,7,12,17‐Tetrakis(pinacolatoboryl) Ni^II porphyrin 5 Ni was synthesized in 75 % yield by Ir‐catalyzed borylation of porphine followed by Ni^II metalation and has been demonstrated to be a useful synthon, giving 2,7,12,17‐tetraaryated Ni^II porphyrins 6 a–d, peripherally octaarylated Ni^II porphyrins 8 a–d, quadruply bridged face‐to‐face non‐offset Ni^II‐porphyrin dimer 12, and cross‐shaped β‐meso singly...

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A Quadruply Bridged Non‐Offset Face‐to‐Face Porphyrin Dimer and Cross‐Shaped Pentameric Porphyrin Tapes Based on 2,7,12,17‐Tetrakis(pinacolatoboryl) Ni^II Porphyrin

Meng Ye, Fangling Deng, Ling Xu, Yutao Rao, more

Angewandte Chemie > 135 > 13 > n/a - n/a

2,7,12,17‐Tetrakis(pinacolatoboryl) Ni^II porphyrin 5 Ni was synthesized in 75 % yield by Ir‐catalyzed borylation of porphine followed by Ni^II metalation and has been demonstrated to be a useful synthon, giving 2,7,12,17‐tetraaryated Ni^II porphyrins 6 a–d, peripherally octaarylated Ni^II porphyrins 8 a–d, quadruply bridged face‐to‐face non‐offset Ni^II‐porphyrin dimer 12, and cross‐shaped β‐meso singly...

article

m‐Benziporphyrin(1.1.0.0)s as a Rare Example of Ring‐Contracted Carbaporphyrins with Metal‐Coordination Ability: Distorted Coordination Structures and Small HOMO‐LUMO Gaps

Le Liu, Fenni Zhang, Ling Xu, Mingbo Zhou, more

Chemistry – A European Journal > 29 > 14 > n/a - n/a

m‐Benziporphyrin(1.1.0.0) and m‐pyreniporphyrin(1.1.0.0) were prepared as ring‐contracted carbaporphyrins. While m‐Benziporphyrin(1.1.0.0) was unstable, m‐pyreniporphyrin(1.1.0.0) was fairly stable. Both of their Pd^II complexes showed distorted coordination structures with extremely short Pd−C bonds. As compared with the reported m‐benziporphyrin Pd^II complexes, these Pd^II complexes showed considerably...

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Facile Formation of Stable Neutral Radicals and Cations from [22]Smaragdyrin BF₂ Complexes

Weikang Deng, Yang Liu, Daiki Shimizu, Takayuki Tanaka, more

Chemistry – A European Journal > 29 > 11 > n/a - n/a

meso‐Trimesityl‐substituted [20]smaragdyrin freebase was synthesized by p‐toluenesulfonic acid catalyzed reaction of 5‐mesityldipyrromethane and 2,14‐dibromodipyrrin in an improved yield of 63 %. Unexpectedly, treatment of the [20]smaragdyrin freebase with BF₃ ⋅ OEt₂ and triethylamine (TEA) gave a stable radical species, in which the BF₂ unit is coordinated at the tripyrrin site, probably by ready...

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Synthesis of Subporphyrin Free Bases

Le Liu, Jinseok Kim, Ling Xu, Yutao Rao, more

Angewandte Chemie International Edition > 61 > 50 > n/a - n/a

B^III subporphyrins are the legitimate ring‐contracted porphyrins consisting of three pyrroles and three meso‐carbons and their chemistry has been extensively developed since the first synthesis in 2006. However, subporphyrin free bases have never been synthesized, despite tremendous attempts to remove the B^III ion. Here we report that Suzuki–Miyaura coupling between α,α′‐diborylated tripyrrane 1 and...

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Synthesis of Subporphyrin Free Bases

Le Liu, Jinseok Kim, Ling Xu, Yutao Rao, more

Angewandte Chemie > 134 > 50 > n/a - n/a

B^III subporphyrins are the legitimate ring‐contracted porphyrins consisting of three pyrroles and three meso‐carbons and their chemistry has been extensively developed since the first synthesis in 2006. However, subporphyrin free bases have never been synthesized, despite tremendous attempts to remove the B^III ion. Here we report that Suzuki–Miyaura coupling between α,α′‐diborylated tripyrrane 1 and...

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Efficient Synthesis of Multiply Seven‐Membered‐Ring Fused Porphyrins by Rhodium‐Catalyzed [5+2] Annulation

Hui Shu, Mengjie Guo, Machongyang Wang, Mingbo Zhou, more

Angewandte Chemie > 134 > 39 > n/a - n/a

Rhodium‐catalyzed reaction of meso‐pyrrol‐2‐yl Ni^II porphyrins with internal alkynes proceeded smoothly to give singly, doubly, and quadruply seven‐membered‐ring fused Ni^II porphyrins as the first example of [5+2] annulation reaction for porphyrin substrates, where the meso‐appended pyrrole unit serves as a directing group. These reactions are operationally quite simple and easy. A plausible reaction...

article

Efficient Synthesis of Multiply Seven‐Membered‐Ring Fused Porphyrins by Rhodium‐Catalyzed [5+2] Annulation

Hui Shu, Mengjie Guo, Machongyang Wang, Mingbo Zhou, more

Angewandte Chemie International Edition > 61 > 39 > n/a - n/a

Rhodium‐catalyzed reaction of meso‐pyrrol‐2‐yl Ni^II porphyrins with internal alkynes proceeded smoothly to give singly, doubly, and quadruply seven‐membered‐ring fused Ni^II porphyrins as the first example of [5+2] annulation reaction for porphyrin substrates, where the meso‐appended pyrrole unit serves as a directing group. These reactions are operationally quite simple and easy. A plausible reaction...

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Search results for: Atsuhiro Osuka

5,18‐Dimesitylorangarin: a Stable Antiaromatic [20]Pentaphyrin(1.0.1.0.0) Displaying Remarkable Oxidative Self‐Coupling Reactions

5,18‐Dimesitylorangarin: a Stable Antiaromatic [20]Pentaphyrin(1.0.1.0.0) Displaying Remarkable Oxidative Self‐Coupling Reactions

[22]Pentaphyrins(2.0.1.1.0) Displaying N‐Fusion, Pyrrole‐Rearrangement, and Dimerization Reactions Upon Oxidation and Metalation

[22]Pentaphyrins(2.0.1.1.0) Displaying N‐Fusion, Pyrrole‐Rearrangement, and Dimerization Reactions Upon Oxidation and Metalation

A Triply Linked Porphyrin‐Norcorrole Hybrid with Singlet Diradical Character

A Triply Linked Porphyrin‐Norcorrole Hybrid with Singlet Diradical Character

Synthesis of Pyrrole‐Sharing Fused Porphyrinoid Hybrids by Post‐fabrication of Ni(II) Porphyrins

Synthesis of Pyrrole‐Sharing Fused Porphyrinoid Hybrids by Post‐fabrication of Ni(II) Porphyrins

Cyclic Azobenzene‐BODIPY Hybrids

Gated Photochromism of Dithienylethene‐Embedded Expanded Calixphyrins

Post‐Installation of Fused Benzoheptagons at the Periphery of NiII Porphyrins: Helical Structures and Conformation‐Adjustable Fullerenes Binding

Oxidation of 3‐Oxo‐N‐Confused Porphyrin with PIFA: Inner and meso Functionalizations

A Quadruply Bridged Non‐Offset Face‐to‐Face Porphyrin Dimer and Cross‐Shaped Pentameric Porphyrin Tapes Based on 2,7,12,17‐Tetrakis(pinacolatoboryl) Ni^II Porphyrin

A Quadruply Bridged Non‐Offset Face‐to‐Face Porphyrin Dimer and Cross‐Shaped Pentameric Porphyrin Tapes Based on 2,7,12,17‐Tetrakis(pinacolatoboryl) Ni^II Porphyrin

m‐Benziporphyrin(1.1.0.0)s as a Rare Example of Ring‐Contracted Carbaporphyrins with Metal‐Coordination Ability: Distorted Coordination Structures and Small HOMO‐LUMO Gaps

Facile Formation of Stable Neutral Radicals and Cations from [22]Smaragdyrin BF₂ Complexes

Synthesis of Subporphyrin Free Bases

Synthesis of Subporphyrin Free Bases

Efficient Synthesis of Multiply Seven‐Membered‐Ring Fused Porphyrins by Rhodium‐Catalyzed [5+2] Annulation

Efficient Synthesis of Multiply Seven‐Membered‐Ring Fused Porphyrins by Rhodium‐Catalyzed [5+2] Annulation

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