FeCl<sub>3</sub>‐Mediated Reaction of 1,4‐Dilithio‐1,3‐dienes with Alkynes Affording Benzene Derivatives

The first catalytic synthesis of cyclic diarylborinic acids is developed using adihydroaminoborane reagent as the boron source.U nlike previously reported methods that use organolithium reagents,t his method allows the easy synthesis of cyclic diarylborinic acids bearing ar ange of functionalities including CN,C O 2 Et, CONEt 2 and NMeCO 2 t Bu. Further-Scheme 1. Cyclic diarylborinic acid 1 and methods for its preparation.Scheme 2. Working hypothesis:two-fold borylation. Scheme 4. Pd-catalyzeda nnulative two-fold Suzuki-Miyaura coupling for the synthesis of benzannulated heterocycles. Reaction conditions: 1i (0.25 mmol), 5 (0.50 mmol), Pd 2 (dba) 3 (0.0038 mmol), t Bu 3 P·HBF 4 (0.0090 mmol), Cs 2 CO 3 (0.83 mmol), H 2 O( 2.5 mmol) in t AmOH (3 mL) at 100 8 8Cfor 24-48 h. Yields of isolated products are shown. [a] Run on a1.0 mmol scale.Scheme 5. Pd-catalyzed two-fold Suzuki-Miyaura coupling using cyclic borinate 1j.Scheme 6. One-pot synthesis of 9-mesityl-9H-boraxanthene 8a. Angewandte Chemie Communications

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Catalytic Double Carbon–Boron Bond Formation for the Synthesis of Cyclic Diarylborinic Acids as Versatile Building Blocks for π‐Extended Heteroarenes

Igarashi

Tobisu

Chatani

2017

Angew Chem Int Ed

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FeCl₃‐Mediated Reaction of 1,4‐Dilithio‐1,3‐dienes with Alkynes Affording Benzene Derivatives

Cited by 10 publications

References 16 publications

Aromatic Ring Construction from Zirconocenes and Titanocenes

Aromatic Ring Construction from Zirconocenes and Titanocenes

Catalytic Double Carbon–Boron Bond Formation for the Synthesis of Cyclic Diarylborinic Acids as Versatile Building Blocks for π‐Extended Heteroarenes

Catalytic Double Carbon–Boron Bond Formation for the Synthesis of Cyclic Diarylborinic Acids as Versatile Building Blocks for π‐Extended Heteroarenes

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FeCl3‐Mediated Reaction of 1,4‐Dilithio‐1,3‐dienes with Alkynes Affording Benzene Derivatives

Cited by 10 publications

References 16 publications

Aromatic Ring Construction from Zirconocenes and Titanocenes

Aromatic Ring Construction from Zirconocenes and Titanocenes

Catalytic Double Carbon–Boron Bond Formation for the Synthesis of Cyclic Diarylborinic Acids as Versatile Building Blocks for π‐Extended Heteroarenes

Catalytic Double Carbon–Boron Bond Formation for the Synthesis of Cyclic Diarylborinic Acids as Versatile Building Blocks for π‐Extended Heteroarenes

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FeCl₃‐Mediated Reaction of 1,4‐Dilithio‐1,3‐dienes with Alkynes Affording Benzene Derivatives