4448-77-5

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 37, p. 508, 1972 DOI: 10.1021/jo00968a045

InChI:InChI=1/C8H17N/c9-7-8-5-3-1-2-4-6-8/h8H,1-7,9H2

Upstream product

• 32730-85-1 cycloheptanecarbonitrile 
• 1459-39-8 cycloheptanecarboxamide 

Downstream Products

• 502-49-8 cycloactanone 
• 25197-50-6 C₂₅H₃₃N₃O₄S 
• 25197-45-9 C₂₃H₂₉N₃O₄S 
• 1026346-99-5 5-((S)-2-{[6-(Cycloheptylmethyl-carbamoyl)-1H-indole-5-carbonyl]-amino}-3-phenyl-propionylamino)-isophthalic acid dibenzyl ester 
• 874569-00-3 (cycloheptylmethyl)[(2-methoxyphenyl)sulfonyl]amine 

Relevant academic research and scientific papers

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

Reduction of selenoamides to amines using SmI2-H2O

Selenoamides are selectively reduced to amines by SmI2 with H2O. The process is general for primary, secondary, and tertiary aryl and alkyl selenoamide substrates and selectively delivers amine products. The reduction proceeds under mild conditions using SmI2 activated by straightforward addition of H2O, and does not require an additional Lewis base additive.

Electron transfer reduction of nitriles using SmI2-Et 3N-H2O: Synthetic utility and mechanism

The first general reduction of nitriles to primary amines under single electron transfer conditions is demonstrated using SmI2 (Kagan's reagent) activated with Lewis bases. The reaction features excellent functional group tolerance and represents an attractive alternative to the use of pyrophoric alkali metal hydrides. Notably, the electron transfer from Sm(II) to CN functional groups generates imidoyl-type radicals from bench stable nitrile precursors.