Highly Efficient Reduction of Aldehydes with Silanes in Water Catalyzed by Silver

Zhenhua Jia; Mingxin Liu; Xingshu Li; Albert S. C. Chan; Chao-Jun Li

doi:10.1055/s-0033-1339660

Synlett, Table of Contents

Synlett 2013; 24(16): 2049-2056
DOI: 10.1055/s-0033-1339660

letter

Highly Efficient Reduction of Aldehydes with Silanes in Water Catalyzed by Silver

Zhenhua Jia

^aDepartment of Chemistry and FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 0B8, Canada Fax: +1(514)3983797 Email: cj.li@mcgill.ca

^bInstitute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006, P. R. of China

,

Mingxin Liu

^aDepartment of Chemistry and FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 0B8, Canada Fax: +1(514)3983797 Email: cj.li@mcgill.ca

,

Xingshu Li

^bInstitute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006, P. R. of China

,

Albert S. C. Chan

^bInstitute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510006, P. R. of China

,

Chao-Jun Li*

^aDepartment of Chemistry and FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 0B8, Canada Fax: +1(514)3983797 Email: cj.li@mcgill.ca

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Abstract

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Abstract

A highly efficient silver-catalyzed chemoselective method for the reduction of aldehydes to their corresponding alcohols in water was developed by using hydrosilanes as reducing agents. The ketones remained essentially inert under the same reaction conditions, thereby providing an additional synthetically useful chemoselectivity.

Key words

aldehyde - reduction - silver - water

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References

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21 Typical Procedure for Reduction of Aldehydes with Silanes in Water Degassed CH₂Cl₂ (0.25 mL) was added to a microwave tube containing the ligand dppf (8.3 mg, 0.015 mmol) and AgPF₆ (2.5 mg, 0.01 mmol) under argon. The resulting suspension was stirred at r.t., until a clear, colorless solution was obtained; then the solvent was removed under high vacuum. Benzaldehyde (1a; 20.3 μL, 0.2 mmol), tripropylsilane (2a; 125 μL, 0.6 mmol), DIPEA (6.9 μL, 0.04 mmol), and H₂O (0.5 mL) were subsequently added. The reaction mixture was stirred for 24 h at 100 °C, then cooled to r.t. and extracted with CH₂Cl₂ (3 × 10 mL). The combined organic phase was concentrated and purified by flash column chromatography on silica gel (hexane–EtOAc, 20:1) to give the desired product 3a as a colorless oil (19.5 mg, 90%). The NMR data are in full agreement with those previously reported in the literature.^{22 1}H NMR (400 MHz, CDCl₃): δ = 7.38–7.35 (m, 4 H), 7.32–7.29 (m, 1 H), 4.69 (s, 2 H), 1.82 (s, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 140.8, 128.5, 127.6, 126.9, 65.3.
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