title: Umpolung Addition of Aldehydes to Aryl Imines.
abstract: One of the classical ways to synthesize amines involves the coupling of carbonyl compounds and imines, either through enolate chemistry or acyl-based carbanion equivalents. We herein report an alternative strategy that is based on the use of aldehydes as alkyl carbanion equivalents in a reductive coupling with aryl imines. A wide array of secondary amines can be synthesized in moderate to high yields. This reaction is mediated by hydrazine and catalyzed by ruthenium(II) complexes, and it tolerates various functional groups, such as esters, amides, and nitriles.
authors.affiliation: Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke St. W., Montreal, Quebec, H3A 0B8, Canada.|Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing, China.
authors.forename: Ning
authors.initials: N
authors.lastname: Chen
authors.affiliation: Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke St. W., Montreal, Quebec, H3A 0B8, Canada.
authors.forename: Xi-Jie
authors.initials: XJ
authors.lastname: Dai
authors.affiliation: Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke St. W., Montreal, Quebec, H3A 0B8, Canada.
authors.forename: Haining
authors.initials: H
authors.lastname: Wang
authors.affiliation: Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke St. W., Montreal, Quebec, H3A 0B8, Canada.
authors.forename: Chao-Jun
authors.initials: CJ
authors.lastname: Li
keywords: aldehydes; hydrazine; imines; reductive addition; ruthenium catalysis