In 2019,Nature Catalysis included an article by Geng, Huihui; Chen, Xiaobei; Gui, Jingjing; Zhang, Yueteng; Shen, Zuyuan; Qian, Pengfei; Chen, Junwei; Zhang, Shilei; Wang, Wei. Formula: C8H8O2. The article was titled 《Practical synthesis of C1 deuterated aldehydes enabled by NHC catalysis》. The information in the text is summarized as follows:
N-heterocyclic carbenes promoted a reversible hydrogen-deuterium exchange reaction with simple aldehydes, which led to a practical approach to synthetically valuable C1 deuterated aldehydes RC(O)D [R = Ph, Bn, CH=CHPh, etc.]. The reactivity of the well-established N-heterocyclic carbene-catalyzed formation of Breslow intermediates from aldehydes was reengineered to overcome the overwhelmingly kinetically favorable benzoin condensation reaction and achieve the critical reversibility to drive the formation of desired deuterated products when an excess of D2O was employed. Notably, this operationally simple and cost-effective protocol served as a general and truly practical approach to all types of 1-D-aldehydes including aryl, alkyl and alkenyl aldehydes and enabled chemoselective late-stage deuterium incorporation into complex, native therapeutic agents and natural products with uniformly high levels (>95%) of deuterium incorporation for a total of 104 tested substrates. The experimental part of the paper was very detailed, including the reaction process of 2-Methoxybenzaldehyde(cas: 135-02-4Formula: C8H8O2)
2-Methoxybenzaldehyde(cas: 135-02-4) is used as a flavor agent in foods including nonalcoholic/alcoholic beverages, baked goods, chewing gum, confections, frozen dairy, fruit ices, hard/soft candy, instant coffee, tea, Jams, jellies, and milk products. It also has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.Formula: C8H8O2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem