Synthesis of new tetrapyrrolic derivatives—porphyrins as dienophiles or dipolarophiles

Abstract

<jats:p> Porphyrins participate as dienophiles in Diels-Alder reactions with ortho-quinodimethanes or pentacene. They can also behave as dipolarophiles in 1,3-dipolar cycloadditions with a range of 1,3-dipoles. These two reaction types were successfully used to synthesize novel chlorins, bacteriochlorins and isobacteriochlorins. </jats:p>

Coordination-Induced Spin-State Switching with Nickel Chlorin and Nickel Isobacteriochlorin

“…This is particular useful for electron deficient porphyins. [4+2] Cycloaddition with o-benzoquinodimethane 9 (Scheme 1, c) and pentacene 10 as well as [3+2] cycloaddition with nitrones 11,12 (Scheme 1, d) and azomethine ylides [13][14][15] (Scheme 1, e) were already presented.…”

Coordination-Induced Spin-State Switching with Nickel Chlorin and Nickel Isobacteriochlorin

“…This is particular useful for electron deficient porphyins. [4+2] Cycloaddition with o-benzoquinodimethane 9 (Scheme 1, c) and pentacene 10 as well as [3+2] cycloaddition with nitrones 11,12 (Scheme 1, d) and azomethine ylides [13][14][15] (Scheme 1, e) were already presented.…”

Recent advances in the functionalization of meso-triarylcorroles via cycloaddition reactions

“…In fact, we have shown that porphyrins can participate in Diels-Alder [29][30][31][32][33][34][35][36][37] and in 1,3-dipolar cycloaddition reactions [38][39][40], affording novel porphyrin, chlorin, bacteriochlorin and isobacteriochlorin derivatives.…”

Nickel-Induced Skeletal Rearrangement of Free Base trans-Chlorins into Monofused NiII-Porphyrins: Synthesis, Structural, Spectral, and Electrochemical Redox Properties

“…The advancement in synthetic methodologies over the past few years brought classical methods to bring functionalized chlorins. , Several methods are available in literature for the synthesis of tetraphenylchlorins (TPCs) from tetraphenylporphyrins (TPPs) . However, there are only a few reports on smooth conversion of functionalized chlorins into porphyrins. , The interconversion of chlorins into porphyrins is of great interest since it opens a new synthetic route to access a wide variety of nonviable β-functionalized porphyrinoids . β-Functionalization via aromatic electrophilic substitution reactions including nitration, formylation, arylation, acylation, and bromination, etc.…”

Coordination-Induced Spin-State Switching with Nickel Chlorin and Nickel Isobacteriochlorin

“…This is particular useful for electron deficient porphyins. [4+2] Cycloaddition with o-benzoquinodimethane 9 (Scheme 1, c) and pentacene 10 as well as [3+2] cycloaddition with nitrones 11,12 (Scheme 1, d) and azomethine ylides [13][14][15] (Scheme 1, e) were already presented.…”

Recent advances in the functionalization of meso-triarylcorroles via cycloaddition reactions

“…In fact, we have shown that porphyrins can participate in Diels-Alder [29][30][31][32][33][34][35][36][37] and in 1,3-dipolar cycloaddition reactions [38][39][40], affording novel porphyrin, chlorin, bacteriochlorin and isobacteriochlorin derivatives.…”

Nickel-Induced Skeletal Rearrangement of Free Base trans-Chlorins into Monofused NiII-Porphyrins: Synthesis, Structural, Spectral, and Electrochemical Redox Properties

“…The advancement in synthetic methodologies over the past few years brought classical methods to bring functionalized chlorins. , Several methods are available in literature for the synthesis of tetraphenylchlorins (TPCs) from tetraphenylporphyrins (TPPs) . However, there are only a few reports on smooth conversion of functionalized chlorins into porphyrins. , The interconversion of chlorins into porphyrins is of great interest since it opens a new synthetic route to access a wide variety of nonviable β-functionalized porphyrinoids . β-Functionalization via aromatic electrophilic substitution reactions including nitration, formylation, arylation, acylation, and bromination, etc.…”

Coordination-Induced Spin-State Switching with Nickel Chlorin and Nickel Isobacteriochlorin

“…This is particular useful for electron deficient porphyins. [4+2] Cycloaddition with o-benzoquinodimethane 9 (Scheme 1, c) and pentacene 10 as well as [3+2] cycloaddition with nitrones 11,12 (Scheme 1, d) and azomethine ylides [13][14][15] (Scheme 1, e) were already presented.…”

Recent advances in the functionalization of meso-triarylcorroles via cycloaddition reactions

“…In fact, we have shown that porphyrins can participate in Diels-Alder [29][30][31][32][33][34][35][36][37] and in 1,3-dipolar cycloaddition reactions [38][39][40], affording novel porphyrin, chlorin, bacteriochlorin and isobacteriochlorin derivatives.…”

Nickel-Induced Skeletal Rearrangement of Free Base trans-Chlorins into Monofused NiII-Porphyrins: Synthesis, Structural, Spectral, and Electrochemical Redox Properties

“…The advancement in synthetic methodologies over the past few years brought classical methods to bring functionalized chlorins. , Several methods are available in literature for the synthesis of tetraphenylchlorins (TPCs) from tetraphenylporphyrins (TPPs) . However, there are only a few reports on smooth conversion of functionalized chlorins into porphyrins. , The interconversion of chlorins into porphyrins is of great interest since it opens a new synthetic route to access a wide variety of nonviable β-functionalized porphyrinoids . β-Functionalization via aromatic electrophilic substitution reactions including nitration, formylation, arylation, acylation, and bromination, etc.…”