New strategy for production of primary alcohols from aliphatic olefins by tandem cross-metathesis/hydrogenation

• Published in: Chinese chemical letters Vol. 31; no. 6; pp. 1525 - 1529
• Main Authors: Jia, Ruilong, Zuo, Zhijun, Li, Xu, Liu, Lei, Dong, Jinxiang
• Format: Journal Article
• Language: English
• Published: NEW YORK Elsevier B.V 01.06.2020; Elsevier; Shanxi University of Traditional Chinese Medicine, Jinzhong 030619, China%Key Laboratory of Coal Science and Technology of Ministry of Education and Shanxi Province, Taiyuan University of Technology, Taiyuan 030024, China%College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, China%College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, China; School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China; College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, China
• Subjects: Aliphatic olefins; Allyl alcohol; Anti-Markovnikov regioselectivity; Chemistry; Chemistry, Multidisciplinary; Cross-metathesis/hydrogenation; Physical Sciences; Primary alcohols; Science & Technology; Allyl alcohol; Cross-metathesis/hydrogenation; Primary alcohols; Aliphatic olefins; Anti-Markovnikov regioselectivity; OXIDATION; ANTI-MARKOVNIKOV HYDRATION; HYDROGENATION; ALKENES; ALLYLIC ALCOHOLS; RH/RU DUAL CATALYST; HYDROFORMYLATION/HYDROGENATION; DERIVATIVES; METATHESIS
• ISSN: 1001-8417; 1878-5964
• DOI: 10.1016/j.cclet.2019.10.001

A new synthetic methodology to produce primary alcohols by tandem cross-metathesis/hydrogenation from terminal aliphatic olefins and biomass-derived allyl alcohol is developed. [Display omitted] Primary alcohols are widely used in industry as solvents and precursors of detergents. The classic methods for hydration of terminal alkenes always produce the Markovnikov products. Herein, we reported a reliable approach to produce primary alcohols from terminal alkenes combining with biomass-derived allyl alcohol by tandem cross-metathesis/hydrogenation. A series of primary alcohol with different chain lengths was successfully produced in high yields (ca. 90%). Computational studies revealed that self-metathesis and hydrogenation of substrates are accessible but much slower than cross-metathesis. This new methodology represents a unique alternative to primary alcohols from terminal alkenes.