Regioselective and Geometrically Controlled Heck 1,1-Diarylation of Unactivated Aliphatic Alkenes

Zhao, Yao; Wang, Shuangqiang; Shao, Huihui; Tan, Xuefei; Chen, Rizhi; Loh, Teck‐Peng; Zhou, Jianrong Steve; Wu, Xiangqian

doi:10.1021/acs.orglett.3c01214

Cited by 6 publications

(1 citation statement)

References 42 publications

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“…In 2023, the above team related the Heck diphenylation of the same substrate leading to 2a2 in 92% yield when performed with phenyl bromide, Pd(PPh 3 ) 4 catalyst, lithium methoxide and para ‐hydroxybenzoic acid in 2,3‐butanediol at 130 °C, while dramatic yield dropping arose under either base‐free or acid‐free conditions (Scheme 3a) [13] . In contrast to the reaction of Scheme 2a, most modifications of the other experimental conditions decreased only moderately 2a2 yield with no or small amount of no‐regioselective Heck and reductive Heck arylation compounds.…”

Section: Domino Diarylationsmentioning

confidence: 99%

Palladium Catalysis: Dependence of the Efficiency of C−C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part C: The Domino Diarylation and Annelation Reactions

Muzart

2023

Adv Synth Catal

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The efficiency of the formation of C–C bonds under palladium catalysis often depends on the nature of the carboxylate ligand and carboxylic acids or alkali metal carboxylates additives. This review which is Part C of a trilogy devoted to the topic, highlights the influence of the carboxylate units on domino diarylation and annelation reactions. The plausible reaction mechanisms are presented with, as far as possible, personal comments.

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Section: Domino Diarylationsmentioning

confidence: 99%

Palladium Catalysis: Dependence of the Efficiency of C−C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part C: The Domino Diarylation and Annelation Reactions

Muzart

2023

Adv Synth Catal

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Nickel-catalyzed reductive 1,1-diarylation of unactivated alkenes with aryl iodides

Wang,

Jin,

Zhou

2024

Org. Chem. Front.

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Remote-Carbonyl-Directed Consecutive Arylation of Terminal Alkenes for the Synthesis of Tetrasubstituted Olefins

Du,

Su,

et al. 2024

Synthesis

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The highly efficient synthesis of all-carbon tetrasubstituted olefins has been concerned for decades, especially for multi-aryl substituted olefins which widely used in functional organic materials and pharmaceuticals. This work presents a carbonyl-directed palladium-catalyzed consecutive arylation of terminal alkenes with aryl iodides under mild conditions, a series of triarylated tetrasubstituted olefins were obtained in moderate yields. Because a weak chelation effect is generally difficult to support such a thorough tri-fold Heck arylation, and the β-trans-selective alkenyl C–H activation cannot be achieved via a twisted endo-metallacyclic intermediate, thus, the key to success is the compatibility between several mechanisms, including Heck, C–H activation and E,Z-isomerization. Here, the judicious selection of a flexible-alkyl-chain-tethered carbonyl group seems to be critical, it provides a proper chelation effect that not only assists a distal alkenyl functionalization or isomerization, but also avoids byproducts caused by other possible β-H elimination or migration. The strategy developed herein greatly streamlines the preparation of the target molecules, and the protocol covers a range of readily available terminal alkenes bearing native directing groups (e.g., aldehyde, ketone and ester), and aryl iodides.

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Regioselective and Geometrically Controlled Heck 1,1-Diarylation of Unactivated Aliphatic Alkenes

Cited by 6 publications

References 42 publications

Palladium Catalysis: Dependence of the Efficiency of C−C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part C: The Domino Diarylation and Annelation Reactions

Palladium Catalysis: Dependence of the Efficiency of C−C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part C: The Domino Diarylation and Annelation Reactions

Nickel-catalyzed reductive 1,1-diarylation of unactivated alkenes with aryl iodides

Remote-Carbonyl-Directed Consecutive Arylation of Terminal Alkenes for the Synthesis of Tetrasubstituted Olefins

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