Direct reductive amination of carbonyl compounds using bis(triphenylphosphine) copper(I) tetrahydroborate

Tetrahedron Letters

Volumn 48, Issue 7, 2007, Pages 1273-1276

  Bhanushali, Mayur J ^a   Nandurkar, Nitin S ^a   Bhor, Malhari D ^a   Bhanage, Bhalchandra M ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Amines; Bis(triphenylphosphine) copper(I) tetrahydroborate; Carbonyl compounds; Reductive amination

Indexed keywords

ALDEHYDE; BIS(TRIPHENYLPHOSPHINE)COPPER TETRAHYDROBORATE; BORIC ACID; CARBONYL DERIVATIVE; CUPROUS ION; FUNCTIONAL GROUP; IMINE; KETONE; NITRILE; NITRO DERIVATIVE; PHOSPHINE DERIVATIVE; REAGENT; REDUCING AGENT; SULFAMIC ACID; TETRAHYDROBORATE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL MODIFICATION; DIRECT REDUCTIVE AMINATION;

EID: 33846286096     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.037     Document Type: Article

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27. Preparation of bis (triphenylphosphine) copper(I) tetrahydroborate: Finely powdered copper(I) chloride (10 g, 0.1 mol) was added to a stirred solution of triphenylphosphine (54 g, 0.205 mol) in chloroform (375 ml) over 5 min. The reaction mixture was stirred until the copper chloride had dissolved (15 min), then treated with a suspension of sodium tetrahydroborate (3.8 g, 0.1 mol) in ethanol (40 ml) and stirred for a further 15 min, and then added to water (75 ml). The chloroform layer was washed with water (2 × 65 ml), dried (magnesium sulphate) and treated with diethyl ether (500 ml). Bis(triphenylphosphine) copper(I) tetrahydroborate precipitated immediately and was collected by filtration and washed with ether to give white needles of 1, mp 172-174 °C.
28. 4 (5 mmol) over a period of 5 min. The reaction mixture was magnetically stirred at room temperature. After completion of the reaction (monitored by TLC), the reaction mixture was filtered and the filtrate was evaporated to yield a crude product, which was purified using silica gel (60-120 mesh) column chromatography with petroleum ether-ethyl acetate as the eluent to afford the pure amine.