Palladium‐Catalyzed Dienylation of Haloalkynes using 2,3‐Butadienyl Acetates: A Facile Access to (1<i>Z</i>)‐1,2‐Dihalo‐ 3‐vinyl‐1,3‐dienes

Chen, Dongxu; Chen, Xiaoyi; Lu, Zenghui; Cai, Haiting; Shen, Jin-Bei; Zhu, Gangguo

doi:10.1002/adsc.201100113

Cited by 34 publications

(8 citation statements)

References 48 publications

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“…15 For example, dihaloalkenes containing two different halogens could undergo cross-coupling reactions in a step-wise manner for the installment of two different molecular fragments. 7,[16][17][18][19][20][21][22][23][24][25][26][27] In this regard, significant efforts have been devoted to the construction of dihaloalkenes. However, the regio-and stereoselective, yet environmentally friendly synthesis of dihaloalkenes with a broad scope is still challenging.…”

Section: Introductionmentioning

confidence: 99%

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

Zeng

Liu

Yang

et al. 2020

Chem

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We describe a catalyst-free 1,2-trans-dihalogenation of alkynes with an unprecedented substrate scope and exclusive regio-and stereoselectivity. This versatile dihalogenation system-a combination of NX 1 S electrophile and alkali metal halide (MX 2 ) in acetic acid-is applicable for diverse categories of alkynes (electron-rich or poor alkynes, internal and terminal alkynes, or heteroatoms such as O-, N-, S-substituted alkynes). The hydrogen bonding donor solvent acetic acid is essential for the in-situ generation of X 1 X 2 electrophile, including ICl, IBr, BrCl, I 2, and Br 2 .

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Section: Introductionmentioning

confidence: 99%

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

Zeng

Liu

Yang

et al. 2020

Chem

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“…β-Heteroatom elimination releases trienes 220 with concomitant regeneration of the catalytic species. 203 …”

Section: Synthetic Utilitymentioning

confidence: 99%

“…Next, the carbopalladation reaction with allenol acetates 218 should form allyl-palladium intermediates II . β-Heteroatom elimination releases trienes 220 with concomitant regeneration of the catalytic species …”

Section: Synthetic Utilitymentioning

confidence: 99%

“…β-Heteroatom elimination releases trienes 220 with concomitant regeneration of the catalytic species. 202 A different mechanistic pathway was proposed to explain the results observed from the reaction of different α-allenols 221 in the presence of catalytic amounts of iron triflate or iron Scheme 37. Palladium-Catalyzed Synthesis of 1-Phosphoryl Trost's research groups have extensively investigated the metal-catalyzed Meyer-Schuster rearrangement of allenols 227 from a different perspective.…”

Section: Enantioenriched Allenolsmentioning

confidence: 99%

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Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

2021

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The allene functionality has participated in one of the most exciting voyages in organic chemistry, from chemical curiosities to a recurring building block in modern organic chemistry. In the last decades, a special kind of allene, namely, allenol, has emerged. Allenols, formed by an allene moiety and a hydroxyl functional group with diverse connectivity, have become common building blocks for the synthesis of a wide range of structures and frequent motif in naturally occurring systems. The synergistic effect of the allene and hydroxyl functional groups enables allenols to be considered as a unique and sole functionality exhibiting a special reactivity. This Review summarizes the most significant contributions to the chemistry of allenols that appeared during the past decade, with emphasis on their synthesis, reactivity, and occurrence in natural products.

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“…Nucleopalladation of alkynes affords the vinyl‐Pd species, which could be captured by a variety of activated alkenes, such as allenes,[28a] allyl acetates,[28b] allyl halides,, [28c] α,β‐unsaturated carbonyl compounds,[28d] norbornene,[28e] and styrene,[23b], [28f] as well as some unactivated alkenes such as long‐chain 1, n ‐enols ( n > 3) , , , . Other polyfunctionalized alkenes, such as enoic acids, are still scarcely explored.…”

Section: Cascade Reactions Triggered By Nucleopalladation In Ilsmentioning

confidence: 99%

Recent Advances in Pd‐Catalyzed Cross‐Coupling Reaction in Ionic Liquids

Yang

et al. 2018

Eur J Org Chem

107

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Ionic liquids (ILs) can behave as green solvents in comparison with conventional organic solvents, but more often they also act as ligands, co‐catalysts, and stabilizing agents both for metal active species and for intermediates of catalytic systems. In this review we have mainly summarized the recent achievements (2013 to the present) in Pd‐catalyzed cross‐coupling in ILs for the assembly of structurally diverse and highly functionalized organic molecules, with the focus on cascade reactions triggered by nucleopalladation, Suzuki coupling, Sonogashira coupling, allylic functionalization, and other types of coupling. The reaction conditions, regio‐ and stereoselectivities, and mechanisms are summarized in detail. We also highlight important and representative examples and synthetic applications of these coupling reactions. We hope that this review will result in further focused research to widen the comprehension and application of ILs in the future.

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Palladium‐Catalyzed Dienylation of Haloalkynes using 2,3‐Butadienyl Acetates: A Facile Access to (1Z)‐1,2‐Dihalo‐ 3‐vinyl‐1,3‐dienes

Cited by 34 publications

References 48 publications

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

Recent Advances in Pd‐Catalyzed Cross‐Coupling Reaction in Ionic Liquids

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