A practical
and efficient synthesis of α-heteroaryl propionic
esters is developed by employing palladium-catalyzed α-heteroarylation
of silyl ketene acetals, forming a wide variety of α-heteroaryl
propionic esters with various substituents and functionalities in
high yields. The success of this transformation is credited to the
development of the bulky P,PO ligand. The method has provided
an efficient synthesis of α-heteroaryl propionic acids.
The Heck reaction between N‐heteroaryl halides and heterocyclic alkenes provides a convenient approach to biologically relevant α‐heteroaryl functionalized heterocycles, yet reactions of this type have been challenging due to strong N‐heteroaryl coordination to palladium metal, which causes catalyst poisoning. In this report, an efficient palladium‐catalyzed Heck reaction between N‐heteroaryl halides and heterocyclic olefins is established, leading to a variety of α‐heteroaryl substituted heterocycles. The method features an unprecedented broad substrate scope and excellent functional group compatibility. The employment of a sterically bulky P, P=O ligand containing an anthryl moiety is crucial for this transformation due to the coordinative unsaturation facilitated by its steric bulkiness. The asymmetric variant of the Heck reaction is achieved with (S)‐DTBM‐SEGPHOS via a cationic palladium pathway, which has enabled an efficient asymmetric synthesis of (S)‐nicotine and its analogues.
The Heck reaction between N-heteroaryl halides and heterocyclic alkenes provides a convenient approach to biologically relevant α-heteroaryl functionalized heterocycles, yet reactions of this type have been challenging due to strong N-heteroaryl coordination to palladium metal, which causes catalyst poisoning. In this report, an efficient palladium-catalyzed Heck reaction between N-heteroaryl halides and heterocyclic olefins is established, leading to a variety of α-heteroaryl substituted heterocycles. The method features an unprecedented broad substrate scope and excellent functional group compatibility. The employment of a sterically bulky P, P=O ligand containing an anthryl moiety is crucial for this transformation due to the coordinative unsaturation facilitated by its steric bulkiness. The asymmetric variant of the Heck reaction is achieved with (S)-DTBM-SEGPHOS via a cationic palladium pathway, which has enabled an efficient asymmetric synthesis of (S)-nicotine and its analogues.
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