Synthesis of Cyclic Anhydrides via Ligand‐Enabled C–H Carbonylation of Simple Aliphatic Acids

Yu, Jin‐Quan; Zhuang, Zhe; Herron, Alastair N.

doi:10.1002/anie.202104645

“…Recently, Yu and co-workers [77] reported the β-C(sp 3 )-H or γ-C(sp 3 )-H carbonylation of free carboxylic acids achieved employing a similar strategy (Scheme 36). The enantioselective carbonylation of free cyclopropanecarboxylic acids was also achieved using a chiral bidentate thioether ligand.…”

Section: Palladium-catalyzed Asymmetric C(spmentioning

confidence: 99%

Palladium-catalyzed enantioselective carbonylation reactions

Peng

¹

,

Liu

²

,

Li

³

et al. 2022

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Carbonylation, one of the most powerful approaches to the preparation of carbonylated compounds, has received significant attention from researchers active in various fields. Indeed, impressive progress has been made on this subject over the past few decades. Among the various types of carbonylation reactions, asymmetric carbonylation is a straightforward methodology for constructing chiral compounds. Although rhodium-catalyzed enantioselective hydroformylations have been discussed in several elegant reviews, a general review on palladium-catalyzed asymmetric carbonylations is still missing. In this review, we summarize and discuss recent achievements in palladium-catalyzed asymmetric carbonylation reactions. Notably, this review’s contents are categorized by reaction type.

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“…The reaction products were isolated as acyclic diester derivatives because of the high sensitivity of anhydrides toward hydrolysis. [78] Moreover, preliminary results of an enantioselective version using the β‐aminothioether ligand L6 have been reported.…”

Section: Transition‐metal‐catalyzed Formal Cycloadditions By C(sp ...mentioning

confidence: 99%

Transition‐Metal‐Catalyzed Annulations Involving the Activation of C(sp³)−H Bonds

Mascareñas

¹

,

Font

²

,

Gulı́as

³

2021

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The selective functionalization of C(sp3)−H bonds using transition‐metal catalysis is among the more attractive transformations of modern synthetic chemistry. In addition to its inherent atom economy, such reactions open unconventional retrosynthetic pathways that can streamline synthetic processes. However, the activation of intrinsically inert C(sp3)−H bonds, and the selection among very similar C−H bonds, represent highly challenging goals. In recent years there has been notable progress tackling these issues, especially with regard to the development of intermolecular reactions entailing the formation of C−C and C−heteroatom bonds. Conversely, the assembly of cyclic products from simple acyclic precursors using metal‐catalyzed C(sp3)−H bond activations has been less explored. Only recently has the number of reports on such annulations started to grow. Herein we give an overview of some of the more relevant advances in this exciting topic.

show abstract

“…Ther eaction products were isolated as acyclicd iester derivatives because of the high sensitivity of anhydrides toward hydrolysis. [78] Moreover,p reliminary results of an enantioselective version using the b-aminothioether ligand L6 have been reported.…”

Section: Formal Cycloadditions With Carbon Monoxidementioning

confidence: 99%

Transition‐Metal‐Catalyzed Annulations Involving the Activation of C(sp³)−H Bonds

Mascareñas

¹

,

Font

²

,

Gulı́as

³

2021

View full text Add to dashboard Cite

The selective functionalization of C(sp3)−H bonds using transition‐metal catalysis is among the more attractive transformations of modern synthetic chemistry. In addition to its inherent atom economy, such reactions open unconventional retrosynthetic pathways that can streamline synthetic processes. However, the activation of intrinsically inert C(sp3)−H bonds, and the selection among very similar C−H bonds, represent highly challenging goals. In recent years there has been notable progress tackling these issues, especially with regard to the development of intermolecular reactions entailing the formation of C−C and C−heteroatom bonds. Conversely, the assembly of cyclic products from simple acyclic precursors using metal‐catalyzed C(sp3)−H bond activations has been less explored. Only recently has the number of reports on such annulations started to grow. Herein we give an overview of some of the more relevant advances in this exciting topic.

show abstract

Synthesis of Cyclic Anhydrides via Ligand‐Enabled C–H Carbonylation of Simple Aliphatic Acids

Abstract: The development of C(sp 3 )-H functionalizations of free carboxylic acids has provided a wide range of versatile CÀ C and CÀY (Y= heteroatom) bond-forming reactions. Addi-Scheme 1. Construction of common structural motifs using a C(sp 3 )-H functionalization strategy.

Cited by 32 publications

References 82 publications

Palladium-catalyzed enantioselective carbonylation reactions

Palladium-catalyzed enantioselective carbonylation reactions

Transition‐Metal‐Catalyzed Annulations Involving the Activation of C(sp³)−H Bonds

Transition‐Metal‐Catalyzed Annulations Involving the Activation of C(sp³)−H Bonds

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Synthesis of Cyclic Anhydrides via Ligand‐Enabled C–H Carbonylation of Simple Aliphatic Acids

Abstract: The development of C(sp 3 )-H functionalizations of free carboxylic acids has provided a wide range of versatile CÀ C and CÀY (Y= heteroatom) bond-forming reactions. Addi-Scheme 1. Construction of common structural motifs using a C(sp 3 )-H functionalization strategy.

Cited by 32 publications

References 82 publications

Palladium-catalyzed enantioselective carbonylation reactions

Palladium-catalyzed enantioselective carbonylation reactions

Transition‐Metal‐Catalyzed Annulations Involving the Activation of C(sp3)−H Bonds

Transition‐Metal‐Catalyzed Annulations Involving the Activation of C(sp3)−H Bonds

Contact Info

Product

Resources

About

Transition‐Metal‐Catalyzed Annulations Involving the Activation of C(sp³)−H Bonds

Transition‐Metal‐Catalyzed Annulations Involving the Activation of C(sp³)−H Bonds