Trimethyltin chloride → HCID 86007195, compound

Participants

Reaction Steps

FIG. 38 depicts the synthesis of 1,8-bis(3,3′-(3,5-dimethylphenyl)-9,9′-diacridyl)naphthalene (32). Suzuki coupling of commercially available 3-bromoaniline, 25, and 3,5-dimethylboronic acid afforded 3-(3,5-dimethyl-phenyl)aniline, 26, in high yields. Treatment of 26 with 2-chlorobenzoic acid 27 gave N-3-(3,5-dimethylphenyl)anthranilic acid, 28, which was converted to 9-bromo-3-(3,5-dimethylphenyl)acridine, 29, using phosphorous oxybromide. Lithiation of 29 at −78° C. followed by stannylation with trimethylstannyl chloride resulted in the formation of 3-(3,5-dimethylphenyl)-9-trimethylstannylacridine, 30, in high yields. Employing stannane 30 and 1,8-dibromonaphthalene 31 in a CuO-promoted Stille coupling yielded 1,8-bis(3,3′-(3,5-dimethylphenyl)-9,9′-diacridyl)naphthalene, 32. We were pleased to find that the anti-isomers of 32 can be separated on a WhelkO-1 column. The CD spectra of the enantiomers of 32 are shown in FIG. 39.

Provenance & Evidence