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Directed ortho -Metalation–Cross-Coupling Strategies. One-Pot Suzuki Reaction to Biaryl and Heterobiaryl Sulfonamides

Cédric Schneider 1 Ellen Broda 2 Victor Snieckus 2
1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 Queen's University [Kingston, Canada]
Abstract : A general synthesis of stable ortho-boropinacolato aryl and heteroaryl sulfonamides by directed ortho-metalation (DoM) and either MeOBPin or i-PrOBpin electrophile quench, 3 → 4, is described. A one-pot metalation–Suzuki cross-coupling procedure for the synthesis of biaryls and heterobiaryls, 3 → 5, and a complementary DoM–Ir-catalyzed boronation sequence (Scheme 6) are delineated.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02380533
Contributor : Cédric Schneider <>
Submitted on : Tuesday, November 26, 2019 - 12:00:47 PM
Last modification on : Monday, December 7, 2020 - 9:44:02 AM

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COMUE-NORMANDIE | INC-CNRS | INSA-ROUEN | UNIROUEN | COBRA | INSA-GROUPE | CNRS | ENSICAEN | UNILEHAVRE | UNICAEN

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Cédric Schneider, Ellen Broda, Victor Snieckus. Directed ortho -Metalation–Cross-Coupling Strategies. One-Pot Suzuki Reaction to Biaryl and Heterobiaryl Sulfonamides. Organic Letters, American Chemical Society, 2011, 13 (14), pp.3588-3591. ⟨10.1021/ol201175g⟩. ⟨hal-02380533⟩

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