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. 2013 Apr 5;15(7):1528-31.
doi: 10.1021/ol400307d. Epub 2013 Mar 15.

Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones

Marc Presset  1 , Daniel Oehlrich, Frederik Rombouts, Gary A Molander
Affiliations

Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones

Marc Presset et al. Org Lett. .

Abstract

Potassium vinyltrifluoroborate was found to be an efficient partner with benzamide derivatives for Rh(III)-catalyzed annulations. 4-Trifluoroboratotetrahydroisoquinolones were generated under mild conditions, affording a regioisomerically complementary substitution pattern to other alkenes in related reactions. These new boron-containing building blocks were derivatized by N-arylations, retaining the boron substituent for further elaboration.

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Figures

Scheme 1
Scheme 1
Syntheses of Isoquinolones by Insertion Reactions
Scheme 2
Scheme 2
Preparative scale
Scheme 3
Scheme 3
Scope of the Insertion of Potassium Vinyltrifluoroborate 2 in Benzhydroxamate Derivatives
Scheme 4
Scheme 4
Selective Buchwald-Hartwig Reactivity
Scheme 5
Scheme 5
Scope of the Buchwald-Hartwig Arylation/Oxidation Sequence
Scheme 6
Scheme 6
Synthesis of Corydaldine 8 using a Rh(III)-Catalyzed Annulation/Protodeborylation Strategy
See this image and copyright information in PMC

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