Extracurricular laboratory: Synthetic route of 40400-13-3

I hope my short article helps more people learn about this compound(1-(Bromomethyl)-2-iodobenzene)Name: 1-(Bromomethyl)-2-iodobenzene. Apart from the compound(40400-13-3), you can read my other articles to know other related compounds.

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, ACS Catalysis called Gold-Catalyzed [5,5]-Rearrangement, Author is Hu, Chao; Farshadfar, Kaveh; Dietl, Martin C.; Cervantes-Reyes, Alejandro; Wang, Tao; Adak, Tapas; Rudolph, Matthias; Rominger, Frank; Li, Jun; Ariafard, Alireza; Hashmi, A. Stephen K., which mentions a compound: 40400-13-3, SMILESS is BrCC1=C(I)C=CC=C1, Molecular C7H6BrI, Name: 1-(Bromomethyl)-2-iodobenzene.

A highly efficient gold-catalyzed cycloisomerization of 1,5-diynes to afford indeno[1,2-c]furans I [R = n-pentyl, Ph, 4-ClC6H4, etc.; R1 = H, 6-OMe 5-F, etc.; R2 = 4-MeC6H4, 2-IC6H4CH2, 3-I-4-MeC6H3, etc.] was developed. Various functional groups were tolerated under the mild reaction conditions, which provided an alternative approach for the synthesis of compounds I. On the basis of mechanistic studies, including crossover experiments, deuterium labeling and computational chem., the product formation proceeded via a formal [5,5]-sigmatropic rearrangement, a yet unknown reactivity pattern in gold catalysis. Instead of a synchronous concerted [5,5]-sigmatropic rearrangement and beyond an asynchronous concerted mode, each involving a single transition state, two energetically low transition states (1.8 and 5.6 kJ/mol) and an intermediate associate of the migrating benzyl cation and the vinyl gold species could be located in the computations.

I hope my short article helps more people learn about this compound(1-(Bromomethyl)-2-iodobenzene)Name: 1-(Bromomethyl)-2-iodobenzene. Apart from the compound(40400-13-3), you can read my other articles to know other related compounds.

Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate