Ligand-controlled, Pd/CuH-catalyzed reductive cross-coupling of terminal alkenes and <i>N</i>-heteroaryl bromides

Seo, Sanghyup; Kim, Donghyeon; Kim, Hyun Woo

doi:10.1039/d1cc04833c

Cited by 11 publications

(3 citation statements)

References 36 publications

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“…More recently, Wu and co‐workers utilized compound 1 a as a ligand to assemble a binuclear yttrium complex 3 which displays notable reactivity in catalyzing a ring‐opening polymerization of rac ‐lactide [4] . In addition, compound 1 a served as a precursor to a series of bicyclic bridgehead phosphoramidite (Briphos) ligands [5] . These reports highlighted the versatility of this scaffold, and therefore an efficient and sustainable synthesis of 1 a and their derivatives would conceivably facilitate numerous novel applications.…”

Section: Introductionmentioning

confidence: 99%

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A Concise Route to Keto‐Bridged Polyphenols by Photo‐Fries Rearrangement in Flow

Lin,

Wang,

Peng

et al. 2024

Chemistry An Asian Journal

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Section: Introductionmentioning

confidence: 99%

“…[4] In addition, compound 1 a served as a precursor to a series of bicyclic bridgehead phosphoramidite (Briphos) ligands. [5] These reports highlighted the versatility of this scaffold, and therefore an efficient and sustainable synthesis of 1 a and their derivatives would conceivably facilitate numerous novel applications.…”

Section: Introductionmentioning

confidence: 99%

A Concise Route to Keto‐Bridged Polyphenols by Photo‐Fries Rearrangement in Flow

Lin,

Wang,

Peng

et al. 2024

Chemistry An Asian Journal

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“…Herein, we demonstrate a ligand-controlled, regio-controlled, and reactive Rh-catalyzed propene hydroformylation. In this study, bicyclic bridgehead phosphoramidite (briphos), − a π-acceptor phosphorus ligand, was optimized to control the regioselectivity of propene hydroformylation toward isobutanal. Additionally, a synergistic ligand effect was found to significantly improve the stability of the Rh/briphos catalyst.…”

Section: Introductionmentioning

confidence: 99%

Synergistic Ligand Effect in Rhodium(I)-Catalyzed Regio-Controlled Propene Hydroformylation

2022

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Propene (propylene) is the most important hydroformylation reactant on an industrial scale, representing approximately 75% of the global consumption of oxo chemicals. Both n-butanal and isobutanal, the products of propene hydroformylation, are valuable precursors, and thus controlling the regioselectivity in this reaction is of academic and industrial interest. In the Rh-catalyzed propene hydroformylation, regioselective reactions have been achieved by a modifying ligand. Although highly normal selective (n/iso > 50) ligands have been reported, iso-selective (n/iso < 1) ligands are limited and more importantly show a significantly reduced activity (TOF < 1000 h–1). Herein, we report a highly reactive and regio-controlled (n/iso = 1) propene hydroformylation enabled by Rh catalysis with a sterically bulky π-acceptor phosphorus (bicyclic bridgehead phosphoramidite (briphos)) ligand. In addition, a briphos/PPh3 ligand combination results in a mixed-ligand Rh(I) complex that shows regioselectivity (n/iso = 1) and high reactivity (TOF = 22,700 h–1) and stability during propene hydroformylation.

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Synthesis of Tetraazamacrocycles by Sequential Palladium‐Catalyzed Allylic Substitution Reactions

et al. 2023

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In this study, we focused on the synthesis of tetraazamacrocycles, an essential class of macrocyclic compounds with applications in coordination chemistry, pharmaceuticals, and catalysis. To accomplish this, we developed a ligand‐controlled palladium‐catalyzed allylic substitution approach using bicyclic bridgehead phosphoramidite (briphos) ligands. This approach allowed us to selectively achieve [1+1] and [1+2] allylic aminations between allylic diols and diamines, while avoiding the formation of cyclic [1+1] products. By combining this approach with sequential acetylation and allylic amination, we successfully synthesized tetraazamacrocycles with ring sizes ranging from 16 to 38. These findings demonstrate the potential of a sequential allylation strategy for synthesizing complex molecules with broad applications in the fields of chemistry, pharmaceuticals, and medicine.

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Ligand-controlled, Pd/CuH-catalyzed reductive cross-coupling of terminal alkenes and N-heteroaryl bromides

Abstract: The reductive cross-coupling of terminal alkenes and N-heterocyclic bromides has been demonstrated by ligand optimization of Pd and CuH catalysis. The optimized ligands are Briphos, a π-acceptor monodentate phosphorus ligand,...

Cited by 11 publications

References 36 publications

A Concise Route to Keto‐Bridged Polyphenols by Photo‐Fries Rearrangement in Flow

A Concise Route to Keto‐Bridged Polyphenols by Photo‐Fries Rearrangement in Flow

Synergistic Ligand Effect in Rhodium(I)-Catalyzed Regio-Controlled Propene Hydroformylation

Synthesis of Tetraazamacrocycles by Sequential Palladium‐Catalyzed Allylic Substitution Reactions

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