Anisole: a further step to sustainable hydroformylation

Abstract

Anisole, a solvent with an impressive sustainability rank, is an excellent alternative for hydroformylation, an industrially important homogeneously catalyzed reaction.

Tandem hydroformylation/isomerization/hydrogenation of bio-derived 1-arylbutadienes for the regioselective synthesis of branched aldehydes

“…entries 2 and 6). Anisole has a much better sustainability rank than toluene and even than p-cymene, [33] and we have recently found it was an excellent solvent for hydroformylation [34]. Although the selectivity for aldehyde 5a in the reaction in anisole was slightly lower than in toluene, it was still reasonably high (85% vs. 91%, cf.…”

“…In a further study, we decided to test other solvents, with higher sustainability rankings than toluene, as a reaction medium for the hydroformylation of 3a. p-Cymene has been successfully employed by us in hydroformylation [34] and metathesis. [35] For the system with p-cymene, the catalytic results were similar to those obtained in toluene ( Table 3, cf.…”

Modular Synthesis of α-Substituted Alkenyl Acetals by a Palladium-Catalyzed Suzuki Reaction of α-Haloalkenyl Acetals with Organoboranes

“…Column chromatography was performed on silica gel to afford the product 2-phenylacrylaldehyde [9] (4) (24.3 mg, 74% yield) as a colorless oil. 1 (1,1-diethoxypropan-2-yl)benzene [10]…”

“…In 2012, the Zhou group reported that α-aryl vinyl acetals could be nicely prepared via selective α arylation of acrolein diethyl acetal under Heck conditions with Pd[(dba)2]/dppf as the catalyst, but a dramatic effect of steric hindrance was observed (eq 5). 10 Although α-substituted alkenyl acetals could be synthesized according to those methods mentioned above, a modular and general protocol is still highly desirable. Inspired by our recent work on the introducing aryl group at α position of various Michael acceptors based on C−C cross-coupling reactions, 11 I envision that straightforward synthesis of α-substituted alkenyl acetals would be feasible via Pd-catalyzed Suzuki arylation and alkylation of vinylhalide (eq 6).…”

Greener, Faster, Stronger: The Benefits of Deep Eutectic Solvents in Polymer and Materials Science

“…The combination of these factors has seen chemists seek alternative solvent systems to address these concerns. Examples of such alternative, more environmentally friendly solvents include dihydrolevoglucosenone (Cyrene TM ) [ 2 ], RodiaSolv© PolarClean [ 3 , 4 ] and bio-derived lignin pyrolysis oil methyl ether [ 5 ], in particular various substituted anisoles [ 6 ].…”