Hydrogen Bond Directed ortho ‐Selective C−H Borylation of Secondary Aromatic Amides

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Abstract: Reported is an iridium catalyst for ortho‐selective C−H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen‐bond interactions. The BAIPy‐Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho‐C−H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety of substrates that differ in electronic and steric properties, and the catalyst tolerates various functional groups. The regioselective C−H borylation catalyst is readily accessible and converts substrates on gram scale with high selectivity and conversion.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Hydrogen Bond Directed ortho ‐Selective C−H Borylation of Secondary Aromatic Amides ; volume:58 ; number:37 ; year:2019 ; pages:13039-13043 ; extent:5
Angewandte Chemie / International edition. International edition ; 58, Heft 37 (2019), 13039-13043 (gesamt 5)

Creator: Bai, Shao‐Tao
Bheeter, Charles B.
Reek, Joost N. H.

DOI: 10.1002/anie.201907366

URN: urn:nbn:de:101:1-2022071209223338403591

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:23 AM CEST

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Associated

Bai, Shao‐Tao
Bheeter, Charles B.
Reek, Joost N. H.

Other Objects (12)

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Iridium‐Catalyzed ortho ‐Selective Borylation of Aromatic Amides Enabled by 5‐Trifluoromethylated Bipyridine Ligands

Iridium‐Catalyzed ortho ‐Selective Borylation of Aromatic Amides Enabled by 5‐Trifluoromethylated Bipyridine Ligands

Iridium‐Catalyzed ortho ‐Selective Borylation of Aromatic Amides Enabled by 5‐Trifluoromethylated Bipyridine Ligands

Iridium‐Catalyzed ortho ‐Selective Borylation of Aromatic Amides Enabled by 5‐Trifluoromethylated Bipyridine Ligands

Acyl‐Directed ortho ‐Borylation of Anilines and C7 Borylation of Indoles using just BBr 3

Acyl‐Directed ortho ‐Borylation of Anilines and C7 Borylation of Indoles using just BBr 3

Acyl‐Directed ortho ‐Borylation of Anilines and C7 Borylation of Indoles using just BBr 3

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Regioselective Aromatic C–H Borylation

Regioselective Aromatic C–H Borylation

Asymmetric γ-Borylation of Aliphatic Amides and Esters

Asymmetric γ-Borylation of Aliphatic Amides and Esters

Air‐Stable Bis‐Cyclometallated Iridium Catalysts for Ortho‐Directed C (sp 2)−H Borylation

Air‐Stable Bis‐Cyclometallated Iridium Catalysts for Ortho‐Directed C (sp 2)−H Borylation

Nickel-catalyzed, silyl-directed, ortho-borylation of arenes via an unusual Ni(II)/Ni(IV) catalytic cycle

Nickel-catalyzed, silyl-directed, ortho-borylation of arenes via an unusual Ni(II)/Ni(IV) catalytic cycle

N–Bpin-Directed Borylation of (Hetero)Aryls

N–Bpin-Directed Borylation of (Hetero)Aryls

The Murai Reaction: ortho-Directed Ruthenium-Catalyzed C–H Alkylation of Aromatic Ketones

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Directed aromatic functionalization

Directed aromatic functionalization

Hydrogen Bond Directed ortho ‐Selective C−H Borylation of Secondary Aromatic Amides

Hydrogen Bond Directed ortho ‐Selective C−H Borylation of Secondary Aromatic Amides

Iridium‐Catalyzed ortho ‐Selective Borylation of Aromatic Amides Enabled by 5‐Trifluoromethylated Bipyridine Ligands

Iridium‐Catalyzed ortho ‐Selective Borylation of Aromatic Amides Enabled by 5‐Trifluoromethylated Bipyridine Ligands

Iridium‐Catalyzed ortho ‐Selective Borylation of Aromatic Amides Enabled by 5‐Trifluoromethylated Bipyridine Ligands

Iridium‐Catalyzed ortho ‐Selective Borylation of Aromatic Amides Enabled by 5‐Trifluoromethylated Bipyridine Ligands

Acyl‐Directed ortho ‐Borylation of Anilines and C7 Borylation of Indoles using just BBr 3

Acyl‐Directed ortho ‐Borylation of Anilines and C7 Borylation of Indoles using just BBr 3

Acyl‐Directed ortho ‐Borylation of Anilines and C7 Borylation of Indoles using just BBr 3

Acyl‐Directed ortho ‐Borylation of Anilines and C7 Borylation of Indoles using just BBr 3

Regioselective Aromatic C–H Borylation

Regioselective Aromatic C–H Borylation

Asymmetric γ-Borylation of Aliphatic Amides and Esters

Asymmetric γ-Borylation of Aliphatic Amides and Esters

Air‐Stable Bis‐Cyclometallated Iridium Catalysts for Ortho‐Directed C (sp 2)−H Borylation

Air‐Stable Bis‐Cyclometallated Iridium Catalysts for Ortho‐Directed C (sp 2)−H Borylation

Nickel-catalyzed, silyl-directed, ortho-borylation of arenes via an unusual Ni(II)/Ni(IV) catalytic cycle

Nickel-catalyzed, silyl-directed, ortho-borylation of arenes via an unusual Ni(II)/Ni(IV) catalytic cycle

N–Bpin-Directed Borylation of (Hetero)Aryls

N–Bpin-Directed Borylation of (Hetero)Aryls

The Murai Reaction: ortho-Directed Ruthenium-Catalyzed C–H Alkylation of Aromatic Ketones

The Murai Reaction: ortho-Directed Ruthenium-Catalyzed C–H Alkylation of Aromatic Ketones

Directed aromatic functionalization

Directed aromatic functionalization

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