Photoexcited Palladium-Catalyzed Synthesis of Chiral Allenes from Alkynes via Isomerization and Deracemization Sequence

A photoexcited palladium-catalyzed synthesis of chiral allenes from alkynes via a sequence of isomerization and deracemization is disclosed. This method offers an efficient and cost-effective approach to produce a wide range of chiral allenes with good enantioselectivities and yields (up to 98% yield and 99% ee). The use of readily available and stable alkynes as starting materials simplifies experimental procedures and broadens the scope of the chiral allene synthesis. DBU plays a crucial dual role in this reaction to effectively facilitate the isomerization of alkynes to allenes and enhance the palladium-catalyzed deracemization under visible light excitation, both of which are vital for the success of the process.

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Publication Details

Journal
ACS Catalysis
Published
2024-10-16
DOI
https://doi.org/10.1021/acscatal.4c04956
Citations
11
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
2.75

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article

Photoexcited Palladium-Catalyzed Synthesis of Chiral Allenes from Alkynes via Isomerization and Deracemization Sequence

Shouyun Yu, Changhua Song
11 citations
ACS Catalysis
Catalytic C–H Functionalization Methods
2.75
article

Photoexcited Palladium-Catalyzed Synthesis of Chiral Allenes from Alkynes via Isomerization and Deracemization Sequence

Shouyun Yu, Changhua Song
article en
11 citations

Abstract

A photoexcited palladium-catalyzed synthesis of chiral allenes from alkynes via a sequence of isomerization and deracemization is disclosed. This method offers an efficient and cost-effective approach to produce a wide range of chiral allenes with good enantioselectivities and yields (up to 98% yield and 99% ee). The use of readily available and stable alkynes as starting materials simplifies experimental procedures and broadens the scope of the chiral allene synthesis. DBU plays a crucial dual role in this reaction to effectively facilitate the isomerization of alkynes to allenes and enhance the palladium-catalyzed deracemization under visible light excitation, both of which are vital for the success of the process.

ACS CatalysisVol. 14(21)
State Key Laboratory of Analytical Chemistry for Life Science (CN), Nanjing University (CN)
National Natural Science Foundation of China, State Key Laboratory of Analytical Chemistry for Life Science
Openalex Percentile: Top 9%
Catalytic C–H Functionalization Methods
2.75
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Photoexcited Palladium-Catalyzed Synthesis of Chiral Allenes from Alkynes via Isomerization and Deracemization Sequence — Shouyun Yu, Changhua Song · ACS Catalysis (2024) | TGRS Research Map | TGRS