Copper-Catalyzed Amidation of Arylboronic Acids with Nitriles

He Huang; Zhong-Tao Jiang; Yang Wu; Cheng-Yan Gan; Jin-Mei Li; Shi-Kai Xiang; Chun Feng; Bi-Qin Wang; Wei-Te Yang

doi:10.1055/s-0035-1561291

Synlett, Table of Contents

Synlett 2016; 27(06): 951-955
DOI: 10.1055/s-0035-1561291

letter

Copper-Catalyzed Amidation of Arylboronic Acids with Nitriles

He Huang

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, P. R. of China Email: xiangsk@hotmail.com Email: wanbiqin1964@126.com

,

Zhong-Tao Jiang

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, P. R. of China Email: xiangsk@hotmail.com Email: wanbiqin1964@126.com

,

Yang Wu

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, P. R. of China Email: xiangsk@hotmail.com Email: wanbiqin1964@126.com

,

Cheng-Yan Gan

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, P. R. of China Email: xiangsk@hotmail.com Email: wanbiqin1964@126.com

,

Jin-Mei Li

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, P. R. of China Email: xiangsk@hotmail.com Email: wanbiqin1964@126.com

,

Shi-Kai Xiang*

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, P. R. of China Email: xiangsk@hotmail.com Email: wanbiqin1964@126.com

,

Chun Feng

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, P. R. of China Email: xiangsk@hotmail.com Email: wanbiqin1964@126.com

,

Bi-Qin Wang*

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu, 610068, P. R. of China Email: xiangsk@hotmail.com Email: wanbiqin1964@126.com

,

Wei-Te Yang

^bDepartment of Public Health, Chengdu Medical College, Chengdu, 610500, P. R. of China

› Author Affiliations

Abstract

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Abstract

A copper-catalyzed amidation of arylboronic acids with nitriles has been developed. This reaction provides an efficient and complementary methodology for the synthesis of various N-arylamides with a broad substrate scope.

Key words

amides - nitriles - amination - copper - catalysis

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References

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9 General Procedure Cu(OTf)₂ (10.8 mg, 0.03 mmol) and phenylboronic acid (1a, 36.6 mg, 0.3 mmol) were placed into a 25 mL Schlenk tube equipped with a magnetic stir bar. To this mixture were added in sequence DCE (1.0 mL, contains 0.1% v/v H₂O), benzonitrile (2a, 36.8 μL, 0.36 mmol), BF₃·OEt₂ (75 μL, 0.6 mmol), and MesI(OAc)₂ (163.8 mg, 0.45 mmol, dissolved in 1.0 mL of DCE containing 0.1% v/v H₂O) with an injection syringe under stirring under an argon atmosphere. After the reaction mixture was stirred for 2 h at 90 °C, TMSOTf (108 μL, 0.6 mmol) was added with an injection syringe. After stirring again for 2 h, H₂O (16 μL, 0.9 mmol) was added, and the reaction was carried out for additional 20 h. The solution was cooled to r.t. and quenched by the addition of H₂O (20 mL) and extracted with CH₂Cl₂ (3 × 10 mL). The organic layer was dried over anhydrous MgSO₄ and concentrated in vacuum. The residue was purified by column chromatography on silica gel (eluent: PE–EtOAc–CH₂Cl₂, 7:1:1) to afford the product 3aa. IR (KBr): ν_max = 3345, 1656, 1579, 1259, 751, 690 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 7.89–7.86 (m, 2 H), 7.84 (s, 1 H), 7.65 (d, J = 7.6 Hz, 2 H), 7.58–7.53 (m, 1 H), 7.52–7.47 (m, 2 H), 7.41–7.36 (m, 2 H), 7.16 (t, J = 7.2 Hz, 1 H) ppm. ¹³C NMR (100 MHz, DMSO-d ₆): δ = 165.5, 139.1, 134.9, 131.5, 128.5, 128.3, 127.6, 123.6, 120.3. ESI-MS: m/z = 198.1 [M + H]⁺.

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