Abstract
A formal enone α-arylation is described. This metal-free transformation relies on the I(III)-mediated skeletal reorganization of silyl enol ethers and features mild conditions, good yields, and high stereoselectivities for β-substituted enones.
Highlights
The development of novel approaches for the synthesis of α-arylated carbonyl compounds remains a topic of interest in synthetic chemistry
Despite the great progress achieved with transition-metalfree approaches, limitations in achievable substitution patterns and low atom economy still remain as drawbacks
In a recently disclosed elegant contribution by Wengryniuk and coworkers on the transition-metal-free α-arylation of enones, the direct C−H α-arylation occurs via the reductive iodonium Claisen rearrangement of in-situ-generated β-pyridinium silyl enol ethers (4) and ArI(O2CCF3)[2] reagents (Scheme 1B).[10]
Summary
Martins − University of Vienna, Institute of Organic Chemistry, 1090 Vienna, Austria; orcid.org/0000-00019143-4434. Daniel Kaiser − University of Vienna, Institute of Organic Chemistry, 1090 Vienna, Austria; orcid.org/0000-00018895-9969. Adriano Bauer − University of Vienna, Institute of Organic Chemistry, 1090 Vienna, Austria; orcid.org/0000-00023376-343X. Irmgard Tiefenbrunner − University of Vienna, Institute of Organic Chemistry, 1090 Vienna, Austria.
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