Decarbonylation through Aldehydic C–H Bond Cleavage by a Cationic Iridium Catalyst

Tomohiko Shirai; Kazuki Sugimoto; Masaya Iwasaki; Ryuki Sumida; Harunori Fujita; Yasunori Yamamoto

doi:10.1055/s-0037-1611802

Synlett, Table of Contents

Synlett 2019; 30(08): 972-976
DOI: 10.1055/s-0037-1611802

letter

Decarbonylation through Aldehydic C–H Bond Cleavage by a Cationic Iridium Catalyst

Tomohiko Shirai *

^aDepartment of Social Design Engineering, National Institute of Technology, Kochi College, 200-1 Monobe, Nankoku, Kochi 783-8508, Japan Email: shirai@kochi-ct.ac.jp

,

Kazuki Sugimoto

^bDepartment of Materials Science and Engineering, National Institute of Technology, Kochi College, 200-1 Monobe, Nankoku, Kochi 783-8508, Japan

,

Masaya Iwasaki

^bDepartment of Materials Science and Engineering, National Institute of Technology, Kochi College, 200-1 Monobe, Nankoku, Kochi 783-8508, Japan

,

Ryuki Sumida

^bDepartment of Materials Science and Engineering, National Institute of Technology, Kochi College, 200-1 Monobe, Nankoku, Kochi 783-8508, Japan

,

Harunori Fujita

^aDepartment of Social Design Engineering, National Institute of Technology, Kochi College, 200-1 Monobe, Nankoku, Kochi 783-8508, Japan Email: shirai@kochi-ct.ac.jp

,

Yasunori Yamamoto

^cDivision of Chemical Process Engineering and Frontier Chemistry Center (FCC), Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kitaku, Sapporo, Hokkaido 060-8628, Japan

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Abstract

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Abstract

We report the decarbonylation of aldehydes through an aldehydic C–H bond cleavage catalyzed by a cationic iridium/bisphosphine catalyst. The reaction proceeds under relatively mild conditions to give the corresponding hydrocarbon products in moderate to high yields. In addition, this cationic iridium catalyst system can be applied to an asymmetric hydroacylation of ketones.

Key words

decarbonylation - iridium catalysis - aldehydes - C–H bond cleavage - asymmetric catalysis - hydroacylation

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References

References and Notes
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15 (Benzyloxy)benzene (2b); Typical ProcedureAn oven-dried sealed tube was charged with [Ir(cod)₂](BAr^F ₄) (0.0125 mmol, 5 mol%), (R)-Xyl-BINAP (0.0138 mmol, 5.5 mol%), and anhyd THF (1.0 mL) under N₂, and the mixture was stirred at r.t. for 30 min. 2-(Phenoxymethyl)benzaldehyde (1b; 0.25 mmol) was added and the resultant mixture was heated at 135 °C for 24 h with stirring. The mixture was then purified by column chromatography (silica gel, hexane) to give a colorless liquid; yield: 16.1 mg (35%).¹H NMR (400 MHz, CDCl₃): δ = 7.27–7.45 (m, 7 H), 6.96–7.00 (m, 3 H), 5.07 (s, 3 H).3-Methyl-2-benzofuran-1(3H)-one (3)An oven-dried two-necked flask with a condenser was charged with [Ir(cod)₂](BAr^F ₄) (0.0125 mmol, 5 mol%), (R)-Xyl-BINAP (0.0138 mmol, 5.5 mol%), and anhyd THF (1.0 mL) under N₂, and the mixture was stirred at r.t. for 30 min. Benzaldehyde 1j (0.25 mmol) was added and the mixture was at 90 °C for 48 h with stirring. The formation of lactone (3) was confirmed by ¹H NMR spectroscopy, and the conversion (57%) was determined through ¹H NMR integration by comparison with the substrate peak.¹H NMR (400 MHz, CDCl₃): δ = 7.91 (d, J = 7.6 Hz, 1 H), 7.68 (td, J = 7.6, 1.2 Hz, 1 H), 7.53 (t, J = 7.6 Hz, 1 H), 7.44 (dd, J = 8.0, 1.2 Hz, 1 H), 5.57 (q, J = 6.8 Hz, 1 H), 1.65 (d, J = 6.4 Hz, 3 H).
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