Abstract
The self-assembly of styrene-type olefins into the corresponding stilbenes was conveniently performed in the Deep Eutectic Solvent (DES) mixture 1ChCl/2Gly under air and in the absence of hazardous organic co-solvents using a one-pot chemo-biocatalytic route. Here, an enzymatic decarboxylation of p-hydroxycinnamic acids sequentially followed by a ruthenium-catalyzed metathesis of olefins has been investigated in DES. Moreover, and to extend the design of chemoenzymatic processes in DESs, we also coupled the aforementioned enzymatic decarboxylation reaction to now concomitant Pd-catalyzed Heck-type C-C coupling to produce biaryl derivatives under environmentally friendly reaction conditions.
Highlights
Following the basis of the Sustainable Development (United Nations, 2015), and trying to confront both the current diminution of crude oil resources and the dramatic environmental difficulties connected with its use, the Chemical Community is making great efforts to employ bio-based feedstock as starting materials instead of non-renewable fossil supplies, attempting to accomplish some of the essential Principles of Green Chemistry (Anastas and Warner, 1998; Matlack, 2001; Lancaster, 2002; Poliakoff et al, 2002; Sheldon et al, 2007)
Ru-catalyzed olefin metathesis is considered as one of the most efficient and reliable synthetic utensils within the organic synthetic toolbox for the selective formation of new C-C bonds, allowing the direct access to organic compounds that would require a larger number of conventional steps for their synthesis (Grubbs, 2003; Hoveyda and Zhugralin, 2007; Grela, 2014)
While olefin metathesis in organic and hazardous Volatile Organic Compounds (VOCs) solvents is nowadays ubiquitous [and even in aqueous media (Lipshutz and Ghorai, 2008; Burtscher and Grela, 2009; Tomasek and Schatz, 2013)], the possibility to carry out ruthenium-catalyzed metathesis of olefins in biorenewable eutectic mixtures has got not precedents, as far as we are aware
Summary
Following the basis of the Sustainable Development (United Nations, 2015), and trying to confront both the current diminution of crude oil resources and the dramatic environmental difficulties connected with its use, the Chemical Community is making great efforts to employ bio-based feedstock as starting materials instead of non-renewable fossil supplies, attempting to accomplish some of the essential Principles of Green Chemistry (Anastas and Warner, 1998; Matlack, 2001; Lancaster, 2002; Poliakoff et al, 2002; Sheldon et al, 2007). On the other hand, during the last decade organic chemists have tried to design cleaner and more efficient one-pot multistep processes as alternative routes to classical step-by-step processes with the concomitant: (i) minimization of the time consumption and chemical waste; (ii) simplification of the practical aspects; and (iii) possibility to cope with sensitive reaction intermediates (no isolation of transiently-formed unstable products is needed; Hayashi, 2016) These one-pot multistep processes typically rely on the employment of the same synthetic organic tool (metal-, bio-, or organo-catalyzed reactions) throughout the transformation, while the corresponding hybrid counterparts combining different catalytic disciplines are still very scarce. SCHEME 2 | BsPAD-catalyzed decarboxylation of p-hydroxycinnamic acids in the 1ChCl/2Gly-water medium
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