Rapid and Controlled Reduction of Acyl Chlorides to Aldehydes Using Pinacolborane

doi:10.6023/cjoc202509007

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (2): 564-569.DOI: 10.6023/cjoc202509007 Previous Articles Next Articles

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频哪醇硼烷快速可控还原酰氯合成醛

刘辉杨^a^,^c, 陈都^a, 苏毅进^a^,^*(), 张鹏^a^,^*(), 刘超^b^,^*()

^a 中国科学院兰州化学物理研究所低碳催化与二氧化碳利用全国重点实验室兰州 730000
^b 南京大学化学化工学院绿色化学与工程研究院配位化学全国重点实验室苏州 215163
^c 中国科学院大学北京 100049

收稿日期:2025-09-05 修回日期:2025-10-07 发布日期:2025-10-23
通讯作者: 苏毅进, 张鹏, 刘超

Rapid and Controlled Reduction of Acyl Chlorides to Aldehydes Using Pinacolborane

Huiyang Liu^a^,^c, Du Chen^a, Yijin Su^a^,^*(), Peng Zhang^a^,^*(), Chao Liu^b^,^*()

^a State Key Laboratory of Low Carbon Catalysis and Carbon Dioxide Utilization, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
^b State Key Laboratory of Coordination Chemistry, Institute of Green Chemistry and Engineering, School of Chemistry and Chemical Engineering, Nanjing University, Suzhou 215163
^c University of Chinese Academy of Sciences, Beijing 100049

Received:2025-09-05 Revised:2025-10-07 Published:2025-10-23
Contact: Yijin Su, Peng Zhang, Chao Liu

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Abstract

A method for the rapid reduction of acyl chlorides to aldehydes was developed using pinacolborane (HBpin) as the reducing agent. The method exhibits excellent generality for both aromatic and aliphatic substrates, affording aldehydes in isolated yields of up to 88% with broad functional group tolerance, including cyano, halogen, alkenyl, ketone, and ester groups. Moreover, the method enables gram-scale aldehyde synthesis and shows high efficiency in reducing in situ generated acyl chlorides, thereby enhancing its synthetic practicality.

Key words: pinacolborane, reduction, acyl chlorides, aldehydes

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Huiyang Liu, Du Chen, Yijin Su, Peng Zhang, Chao Liu. Rapid and Controlled Reduction of Acyl Chlorides to Aldehydes Using Pinacolborane[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 564-569.

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Fig. & Tab. 4

Scheme 1. Strategies for the synthesis of aldehydes

Entry	x	Yield^b/%
1	0.0	N.D.
2	0.5	24
3	1.0	41
4	1.5	93
5	2.0	96
6	2.2	93
7	2.5	94

Table 1. Optimization of the reaction conditionsa

Scheme 2. Substrate scope a Reaction conditions: a (1.0 mmol, 1.0 equiv.), DMAP (2.0 mmol, 2.0 equiv.), HBpin (1.0 mmol, 1.0 equiv.), yields are based on isolated products. b Reaction conditions: b (1.0 mmol, 1.0 equiv.), N,N-dimethylformamide (DMF) (cat. 2 drops), (COCl)2 (1.1 mmol, 1.1 equiv.), 4-(piperidin-1-yl)pyridine (PPDP) (2.7 mmol, 2.7 equiv.), HBpin (1.0 mmol, 1.0 equiv.), yields are based on isolated products. c Reaction conditions: b (0.5 mmol, 1.0 equiv.), yields are based on isolated products.

Scheme 3. Synthetic applications aReaction conditions: benzoyl chloride (10 mmol, 1.0 equiv.), DMAP (20 mmol, 2.0 equiv.), HBpin (10 mmol, 1.0 equiv.). Yields are based on isolated products.

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频哪醇硼烷快速可控还原酰氯合成醛

Rapid and Controlled Reduction of Acyl Chlorides to Aldehydes Using Pinacolborane

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