Safety of 3,4-Dimethoxybenzaldehyde. In 2021 ACS CATAL published article about TO-HEAD DIMERIZATION; NONAROMATIC CATECHOL BIOISOSTERES; AZA-CLAISEN REARRANGEMENT; TERMINAL ARYL ALKYNES; CONJUGATED ENYNES; SELECTIVE DIMERIZATION; CATALYZED DIMERIZATION; PALLADIUM COMPLEXES; TAIL DIMERIZATION; PALLADACYCLE in [Pfeffer, Camilla; Wannenmacher, Nick; Frey, Wolfgang; Peters, Rene] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany in 2021, Cited 69. The Name is 3,4-Dimethoxybenzaldehyde. Through research, I have a further understanding and discovery of 120-14-9.
Enynes are important motifs in bioactive compounds. They can be synthesized by alkyne-alkyne couplings for which a number of mechanisms have been suggested depending on catalyst type and dominant product isomers. Regarding bimetallic pathways, hydrometalations and anti-carbopalladations have been discussed to account for the formation of geminally substituted and (Z)-configured enynes, respectively. Here we report a bimetallic alkyne-alkyne coupling that yields (E)-configured enynes. An unusual type of acetylide Pd bridging was found in putative catalytic intermediates which is arguably responsible for the regio- and stereochemical reaction outcome. Mechanistic studies suggest that a double mu-kappa:eta(2) acetylide bridging enables a bimetallic syn-carbometalation. Interestingly, depending on the reaction conditions, it is also possible to form the geminal regioisomer as major product with the same catalyst. This regiodivergent outcome is explained by bi-versus monometallic reaction pathways.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles