In 2022,Yimyaem, Jirapat; Chantana, Chayamon; Boonmee, Suthimon; Jaratjaroonphong, Jaray published an article in Synlett. The title of the article was 《Expedient Access to Indolyl-Substituted Tri- and Diarylmethanes and (±)-Colletotryptin E by Silica Sulfuric Acid Catalyzed Transindolylation》.Name: 2-(Benzyloxy)acetaldehyde The author mentioned the following in the article:
An expedient access to a series of nonsym. bis(indolyl)methanes (BIMs) through transindolylation of readily available sym. 3,3′-BIMs with various indoles catalyzed by silica-supported sulfuric acid has been established. This approach not only provides a useful strategy for the synthesis of structurally diverse BIMs, but also provides examples of nucleophilic substitution of BIMs with aromatic and nonaromatic π-systems, leading to a library of indolyl-substituted tri- and diarylmethanes. Moreover, this method was successfully applied in the first total synthesis of the 2,3′-BIM alkaloid (±)-colletotryptin E (I) in three steps with an overall yield of 46%. The features of this procedure include a metal-free process, an inexpensive and environmentally friendly catalyst, mild reaction conditions, broad functional-group tolerance, good yields, and gram-scalable preparations In the experiment, the researchers used many compounds, for example, 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Name: 2-(Benzyloxy)acetaldehyde)
2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).Name: 2-(Benzyloxy)acetaldehyde
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem