Ruthenium‐Catalyzed Reductive Amidation without an External Hydrogen Source. Issue 4 (31st January 2018)

• Record Type: Journal Article
• Authors: Yagafarov, Niyaz Z.; Muratov, Karim M.; Biriukov, Klim; Usanov, Dmitry L.; Chusova, Olga; Perekalin, Dmitry S.; Chusov, Denis
• Is Part Of: European journal of organic chemistry. Issue 4(2018)
• Page Start: 557
• Page End: 563
• Publication Date: 2018-01-31
• Subjects: Amides -- Aldehydes -- Ruthenium -- Homogeneous catalysis -- Reductive amidation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701527
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A catalytic reaction between aldehydes and primary amides that leads to N ‐alkylated amides was investigated. The developed protocol employs carbon monoxide as a deoxygenative agent and, therefore, avoids the use of an external hydrogen source. Cyclopentadienyl ruthenium complexes provided excellent catalytic efficiency and could be used with loadings as low as 0.5–1 mol‐%. A representative number of secondary amides were successfully prepared in yields of 70–84 %. Abstract : A catalytic system for the atom‐economical Ru‐catalyzed reductive amidation of aldehydes was developed. A cyclopentadienyl ruthenium catalyst was employed in this process with loadings as low as 0.5–1 mol‐%, and carbon monoxide was used as the deoxygenative agent. A number amides and aromatic aldehydes were able to successfully afford the corresponding secondary amide in yields of 79–84 %.