37617-03-1Relevant articles and documents
New strategy for production of primary alcohols from aliphatic olefins by tandem cross-metathesis/hydrogenation
Jia, Ruilong,Zuo, Zhijun,Li, Xu,Liu, Lei,Dong, Jinxiang
supporting information, p. 1525 - 1529 (2019/11/11)
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. 90percent). 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.
Zinc-catalyzed chemoselective reduction of esters to alcohols
Das, Shoubhik,Moeller, Konstanze,Junge, Kathrin,Beller, Matthias
experimental part, p. 7414 - 7417 (2011/08/05)
Economical alcohols! A general and chemoselective catalytic reduction of esters to alcohols using inexpensive zinc acetate and silanes has been developed. The operational simplicity and the high functional group tolerance, without the need for protecting and deprotecting steps, make this procedure particularly attractive for organic synthesis. Copyright
The cross-metathesis of methyl oleate with c/s-2-butene-1,4-diyl diacetate and the influence of protecting groups
Behr, Arno,Gomes, Jessica Perez
scheme or table, p. 1 - 8 (2011/03/22)
Background: α,ω-Difunctional substrates are useful intermediates for polymer synthesis. An attractive, sustainable and selective (but as yet unused) method in the chemical industry is the oleochemical cross-metathesis with preferably symmetric functionalised substrates. The current study explores the cross-metathesis of methyl oleate (1) with cis-2-butene-1,4-diyl diacetate (2) starting from renewable resources and quite inexpensive base chemicals. Results: This cross-metathesis reaction was carried out with several phosphine and N-heterocyclic carbene ruthenium catalysts. The reaction conditions were optimised for high conversions in combination with high cross-metathesis selectivity. The influence of protecting groups present in the substrates on the necessary catalyst loading was also investigated. Conclusions: The value-added methyl 11-acetoxyundec-9-enoate (3) and undec-2-enyl acetate (4) are accessed with nearly quantitative oleochemical conversions and high cross-metathesis selectivity under mild reaction conditions. These two cross-metathesis products can be potentially used as functional monomers for diverse sustainable polymers.
