Recent advances in transition-metal-catalyzed directed C–H alkenylation with maleimides

Liu, Shuang‐Liang; Ye, Changchun; Wang, Xiaoge

doi:10.1039/d2ob00604a

Cited by 33 publications

(9 citation statements)

References 48 publications

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“…In other words, the pyrazolidinonyl moiety is creatively used as a traceless bifunctional DG, eventually merging into the final product. Inspired by these elegant pioneering studies and as a continuation of our own interest in developing efficient and sustainable synthetic methods by taking advantage of the inert C-H bond activation strategy, , we have explored the reaction of 1-phenylpyrazolidinones with maleimides. , From this study, a selective synthesis of succinimide spiro pyrazolo[1,2- a ]pyrazolones or succinimide-fused pyrazolidinonylcinnolines from the same starting materials was successfully established. Herein, we would like to report the detailed results obtained in this aspect.…”

Section: Introductionmentioning

confidence: 99%

Selective Construction of Spiro or Fused Heterocyclic Scaffolds via One-pot Cascade Reactions of 1-Arylpyrazolidinones with Maleimides

Zhang

et al. 2022

J. Org. Chem.

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Presented herein is a controllable selective construction of spiro or fused heterocyclic scaffolds through the onepot cascade reactions of 1-phenylpyrazolidinones with maleimides. To be specific, succinimide spiro pyrazolo[1,2-a]pyrazolones were effectively formed via [4 + 1] spiroannulation of 1-phenylpyrazolidinones with maleimides through simultaneous C(sp 2 )-H bond activation/functionalization and intramolecular cyclization along with the traceless fusion of the pyrazolidinonyl unit into the final product. In this reaction, air acts as a cost-effective and environmentally sustainable oxidant to assist the regeneration of the Rh(III) catalyst. Alternatively, succinimide-fused pyrazolidinonylcinnolines were formed from the same starting materials through an initial [4 + 1] spiroannulation followed by basepromoted skeleton rearrangement of the in situ formed spiro product without isolation. Notable features of these protocols include easily tunable selectivity, broad substrate scope, cost-effective and sustainable oxidant, excellent atom economy, and facile scalability.

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Section: Introductionmentioning

confidence: 99%

Selective Construction of Spiro or Fused Heterocyclic Scaffolds via One-pot Cascade Reactions of 1-Arylpyrazolidinones with Maleimides

Zhang

et al. 2022

J. Org. Chem.

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“…However, alkenes that have multiple reactive sites, such as maleimides, have not been used in the synthesis of indolizines, since the amide groups of maleimides are also highly reactive, making the selectivity for the C=C double bond difficult to control. Therefore, how to achieve selectivity for the C=C bond over the amide represents a significant challenge to overcome but one that has practical implications in synthetic chemistry.…”

Section: Introductionmentioning

confidence: 99%

Cu-Catalyzed Oxidative [3 + 2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones

Zhao

et al. 2022

J. Org. Chem.

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A novel protocol for the construction of highly functionalized indolizine derivatives, that is, 1H-pyrrolo[3,4-b]indolizine-1,3-diones (PIZDOs, 3) from 2-(pyridine-2-yl)acetates and maleimides via a regioselective oxidative [3 + 2] annulation was developed. The cascade oxidative reaction was enabled by heating a mixture of the two substrates in the presence of Ag2CO3 as an oxidant and Cu(OAc)·H2O as a catalyst in chlorobenzene. Consequently, a series of PIZDOs 3 were synthesized with high regioselectivity in moderate yields. This protocol can be used in the synthesis of functionalized PIZDOs via the one-pot oxidative annulation reaction rather than through multistep reactions, which is suitable for both combinatorial and parallel syntheses of PIZDOs.

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“…In these transformations, mostly the desired products were obtained as hydroarylated products via 1,4‐conjugate addition (Michael‐type reaction), [6a–b] spiro‐products [4+1, spiro cyclization] [6c–d] and annulated products [4+2, annulation] (Scheme 1, eq i) [6e,f] . However, there are only a few reports for the formation of Heck‐type alkenylated products involving the maleimides as coupling partners [2g,7] . Heck‐type reactions using maleimide as a coupling partner are in general more challenging as the reaction mostly proceeds via in situ generations of rigid bicyclic species through the activation of C−H bonds, which lacks β‐hydrogen in syn‐periplanar position to the metal center and therefore β‐hydride elimination becomes a difficult task.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3‐Arylacetamides Substituted Maleimide Via Weakly Coordinating Acetamide Assisted Cross‐dehydrogenative Coupling and Their Photophysical Studies

Mishra

Kumar

2022

Eur J Org Chem

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Maleimides serve as an important synthetic precursor for various organic transformation reactions. However, maleimides have been rarely employed as coupling partners for the direct synthesis of 3‐aryl substituted maleimides via oxidative Heck‐type reaction, due to the lack of β‐hydrogen at the syn‐periplanar position. Therefore, herein, we report an efficient and highly selective synthesis of 3‐arylacetamide incorporated maleimides through the cross‐dehydrogenative coupling process using the simple and native primary acetamide as a weakly directing group with Pd(II)‐catalysis conditions. This reaction furnishes 3‐arylated maleimide derivatives in good yields with high functional group tolerance. Furthermore, 3‐arylated maleimides were transformed into synthetically important derivatives. Based on preliminary control experiments, a probable reaction mechanism has been proposed for the distal C−H bond functionalization reaction. Interesting photophysical properties of the synthesized products were also observed.

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Recent advances in transition-metal-catalyzed directed C–H alkenylation with maleimides

Abstract: Transition-metal-catalyzed directed C-H alkenylation with maleimides has attracted much attention in recent years. As maleimide core moieties are present in various natural products and pharmaceuticals. In addition, these derivatives can...

Cited by 33 publications

References 48 publications

Selective Construction of Spiro or Fused Heterocyclic Scaffolds via One-pot Cascade Reactions of 1-Arylpyrazolidinones with Maleimides

Selective Construction of Spiro or Fused Heterocyclic Scaffolds via One-pot Cascade Reactions of 1-Arylpyrazolidinones with Maleimides

Cu-Catalyzed Oxidative [3 + 2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones

Synthesis of 3‐Arylacetamides Substituted Maleimide Via Weakly Coordinating Acetamide Assisted Cross‐dehydrogenative Coupling and Their Photophysical Studies

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