Palladium-Catalyzed Ring Opening of Cyclobutanones with Carbon- and Heteroatom-Centered Nucleophiles

Yusuke Ano; Daichi Takahashi; Kazumune Yo; Ryosuke Nagamune; Naoto Chatani

doi:10.1055/s-0042-1751474

Synlett, Table of Contents

Synlett 2023; 34(20): 2486-2490
DOI: 10.1055/s-0042-1751474

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Special Issue Dedicated to Prof. Hisashi Yamamoto

Palladium-Catalyzed Ring Opening of Cyclobutanones with Carbon- and Heteroatom-Centered Nucleophiles

Yusuke Ano∗

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

,

Daichi Takahashi

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

,

Kazumune Yo

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

,

Ryosuke Nagamune

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

,

Naoto Chatani

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

^bResearch Center for Environmental Preservation, Osaka University, 2-4 Yamadaoka, Suita, Osaka 565-0871, Japan

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Abstract

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Dedicated to Professor Hisashi Yamamoto for his 80^th birthday.

Abstract

The transformation of cyclobutanones into acyclic carbonyl compounds through a Pd-catalyzed C–C bond cleavage is reported. The use of an N-heterocyclic carbene ligand efficiently promoted the ring opening and functionalization of various cyclobutanones, not only with alcohols, but also with N-centered nucleophiles, such as aniline or amide derivatives. Cyclobutanones were also found to react with arylboronic esters, resulting in the production of acyclic aryl ketones.

Key words

palladium catalysis - N-heterocyclic carbenes - cyclobutanones - C–C bond activation - ring opening - arylboronate esters

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References

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14a Benzyl 3-Phenylbutanoate (3); Typical Procedure: In a glove box, an oven-dried screw-capped vial (10 mL) equipped with a magnetic stirrer bar was charged sequentially with (IPr)Pd(allyl)Cl (8.6 mg, 0.015 mmol), t-BuOK (1.7 mg, 0.015 mmol), and toluene (0.75 mL), and the mixture was stirred for a few minutes at r.t. Cyclobutanone 1 (0.3 mmol), benzyl alcohol (2; 65 mg, 0.6 mmol), and toluene (0.75 mL) were then added, and the vial was sealed with a Teflon cap and heated at 90 °C with stirring for 20 h. The resulting mixture was filtered through a pad of Celite and eluted with EtOAc. The eluent was concentrated under a reduced pressure and the residue was purified by column chromatography (silica gel) to give a pale-yellow oil; yield: 62.5 mg (80%); R_f = 0.47 (hexane–EtOAc, 5:1). IR (ATR): 3031 , 2964 , 1733 , 1453 , 1265 , 1154 ¹H NMR (400 MHz, CDCl₃): δ = 7.36–7.18 (c, 10 H), 5.05 (s, 2 H), 3.35–3.25 (m, 1 H), 2.68 (dd, J = 15.1, 7.1 Hz, 1 H), 2.61 (dd, J = 15.1, 8.0 Hz, 1 H), 1.30 (d, J = 6.9 Hz, 3 H). ¹³C NMR (101 MHz, CDCl₃): δ = 172.4, 145.7, 136.0, 128.6, 128.3, 126.9, 126.6, 66.3, 43.0, 36.7, 22.0 (two peaks were obscured due to the overlap of the signals). MS (EI) m/z (%) = 163 (39) [M–Bn]⁺, 121 (100), 117 (19), 105 (46), 103 (11), 91 (100), 79 (17), 78 (11), 77 (23), 65 (20), 51 (10). HRMS (DART): m/z [M + H]⁺ calcd for C₁₇H₁₉O₂: 255.1380; found: 255.1369.

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