Iridium(I)-Catalyzed C-C and C-N Bond Formation Reactions via the Borrowing Hydrogen Strategy
Makaleler > Tam Makale · 2019
Yazarlar: Sertac Genc, Burcu Arslan, Süleyman GÜLCEMAL, Salih Günnaz, BEKİR ÇETİNKAYA, Derya GÜLCEMAL
JOURNAL OF ORGANIC CHEMISTRY, SCI Expanded İndekslerine Giren Dergi, Uluslararası, 2019, cilt 84, ss 6286-6297
Özet
Iridium(I) complexes having an imidazol-2-ylidene ligand with benzylic wingtips efficiently catalyzed the beta-alkylation of secondary alcohols with primary alcohols and acceptorless dehydrogenative cyclization of 2-aminobenzyl alcohol with ketones through a borrowing hydrogen pathway. The beta-alkylated alcohols, including cholesterol derivatives, and substituted quinolines were obtained in good yields by using a minute amount of the catalyst with a catalytic amount of NaOH or KOH under the air atmosphere, liberating water (and H-2 in the case of quinoline synthesis) as the sole byproduct. Notably, this system demonstrated turnover numbers of 940 000 (for beta-alkylation of secondary alcohols with primary alcohols by using down to 0.0001 mol % = 1 ppm of the catalyst) and 9200 (acceptorless dehydrogenative cyclization of 2-aminobenzyl alcohol with ketones).