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, 16 (6), 1574-7

Boron-Heck Reaction of Cyclic Enaminones: Regioselective Direct Arylation via Oxidative palladium(II) Catalysis

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Boron-Heck Reaction of Cyclic Enaminones: Regioselective Direct Arylation via Oxidative palladium(II) Catalysis

Yong Wook Kim et al. Org Lett.

Abstract

An oxidative boron-Heck reaction of cyclic enaminones with arylboronic acids is reported. This protocol provides a regioselective arylation at the C6 position of cyclic enaminones. When an N-carbamylated cyclic enaminone was employed, a switch to a conjugate addition reaction occurred in the presence of acid.

Figures

Scheme 1
Scheme 1. Utility of Cyclic Enaminones
Scheme 2
Scheme 2. Regioselective Arylation of Cyclic Enaminones
Scheme 3
Scheme 3. Scope of the Reaction
Reaction conditions: cyclic enaminone (0.2 M), arylboronic acid (3 equiv), Pd(OAc)2 (10 mol %), ligand (11 mol %), oxygen (balloon pressure).
Figure 1
Figure 1
Proposed reaction mechanisms.
Scheme 4
Scheme 4. Formal Synthesis of Lasubine II

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