Divergent Synthesis of Pentacyclic Isoindolinones Enabled by Sequential Insertion of Two Different Isocyanides and Acid Promoted Cyclization of Ketenimines

Organic Letters, Год журнала: 2023, Номер 25(12), С. 2041 - 2046

Опубликована: Март 22, 2023

A palladium-catalyzed multicomponent reaction involving o-bromobenzaldehydes and two different isocyanides was developed to assemble series of isoindolinones with spiroindolenine or azepinoindole skeletons. This sequential insertion features mild conditions, a wide substrate scope, high efficiency. Preliminary mechanistic study indicated that the difference in steric hindrance between isocyanide components is crucial when regulating sequence, whereas ligand also played an important role during whole process.

Язык: Английский

---

Pd-catalyzed imine-directed one-pot access to polysubstituted pyrrolesviatandem triple isocyanide insertion/aza-Nazarov cyclization reactions

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(13), С. 3252 - 3258

Опубликована: Янв. 1, 2023

A novel one-pot method for synthesizing polysubstituted pyrrole derivatives via three-component reactions of alkenyl bromides, amines, and isocyanides is reported by Pd catalysis, without additional ligands, with the orderly insertion three isocyanide molecules.

Язык: Английский

---

Reactions Involving Multiple Isocyanide Insertions

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(7), С. 926 - 947

Опубликована: Фев. 2, 2023

Abstract Isocyanides (isonitriles or carbylamine) have been intensively used in organic synthesis to prepare a diverse variety of N‐heterocycles on the basis carbene‐like reactivity their divalent carbon atom. participate reactions involving one, two, more isocyanides. Compared popularity single isocyanide reactions, few examples two isocyanides reported. In this review, we categorized and classified literatures especially double insertions under metal‐catalyzed metal‐free conditions from 2014 2022. magnified image

Язык: Английский

---

C–H functionalization enabled by multiple isocyanides

Chemical Society Reviews, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

This review outlines in detail strategies for state-of-the-art synthetic routes and demonstrates various interactions from the synergistic combination of C–H functionalization with multiple isocyanides to establish complicated reactions.

Язык: Английский

---

Catalytic asymmetric interrupted Attanasi reaction: access to fused 2,3-dihydropyrroles with vicinal quaternary carbons

Chemical Communications, Год журнала: 2023, Номер 59(52), С. 8103 - 8106

Опубликована: Янв. 1, 2023

The first catalytic asymmetric interrupted Attanasi reaction has been established. Under the catalysis of a bifunctional organocatalyst, condensation cyclic β-keto esters with azoalkenes readily occurred, delivering variety bicyclic fused 2,3-dihydropyrroles vicinal quaternary stereogenic centers in good yields and to excellent enantioselectivities (27 examples, up 96% yield 95% ee).

Язык: Английский

---

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

ChemistrySelect, Год журнала: 2023, Номер 8(6)

Опубликована: Фев. 8, 2023

Abstract This review aims to collect and analyze recent results with respect the use of varied palladium preparations in synthesis five‐membered nitrogen heterocycles including condensed derivatives. Results have been selected focus on studies last three years. Furthermore, a common feature all methods treated here is that nitrogen‐containing ring formed via closing appropriate starting materials. Selected examples discussed will reveal plethora products from small monocycles multi‐ring systems can be successfully accessed. Major features are wide product ranges, high yields stereoselectivities often achieved under mild reaction conditions.

Язык: Английский

---

Rh-catalysed divergent synthesis of polysubstituted pyrroles from α,β-unsaturated ketones via selective single or double insertion of isocyanides

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(22), С. 5559 - 5567

Опубликована: Янв. 1, 2023

A novel divergent synthetic method for polysubstituted pyrroles from isocyanides and α,β-unsaturated ketones in the presence of a rhodium catalyst bis(pinacolato)diboron (B 2 pin ) is described here.

Язык: Английский

---

Photoinduced radical cascade brominative addition/spirocyclization of N-arylpropiolamides and CBr4 with O2 as oxidant

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

A visible-light-induced brominated spirocyclization of N-arylpropiolamides and CBr4 for the synthesis 3-bromo-azaspiro[4,5]trienones is reported here. This process allows formation C-Br, C-C, C=O bonds in a single reaction via cascade radical addition/ipso-cyclization/oxidative dearomatization sequence. protocol also features high functional group tolerance, operational simplicity use molecular oxygen as an oxidant well sustainable photocatalyst- additive-free conditions at room temperature. Meanwhile, presented straightforward strategy has been applied to several biologically active compounds.

Язык: Английский

---

Hydrogen bond-promoted regio- and stereoselective synthesis of isoindoline derivatives through Pd-catalyzed isocyanide insertion reaction involving aziridines

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(6), С. 1775 - 1781

Опубликована: Янв. 1, 2024

We have successfully demonstrated an efficient and practical Pd-catalyzed reaction between aziridine isocyanide, leading to the synthesis of isoindoline derivatives in moderate good yields.

Язык: Английский

---

[1,2]‐Phospha‐Brook Rearrangement‐Initiated Palladium‐Catalyzed Cyclization Reaction of Isocyanides and o‐Bromobenzaldehydes: Access to 2H‐Isoindole‐1‐carboxamides and 2H‐Isoindole‐1‐carbonitriles

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 20, 2024

Comprehensive Summary Herein, a [1,2]‐phospha‐Brook rearrangement‐initiated palladium‐catalyzed cyclization reaction for base‐controlled selective synthesis of 2 H ‐isoindole‐1‐carboxamide and ‐isoindole‐1‐carbonitrile derivatives has been described. This strategy features double isocyanide insertion, efficient bond combinations, simple operation conditions. Mechanistic studies show that the rearrangement is key step in this reaction. protocol offers novel concise ‐isoindole derivatives.

Язык: Английский

---