Details

Autor(en) / Beteiligte

• Snelling, Rachel A.
• Amberchan, Gabriella
• Resendez, Angel
• Murphy, Chris L.
• Porter, Lauren
• Singaram, Bakthan

Titel

Diisobutylaluminum borohydride: An efficient reagent for the reduction of tertiary amides to the corresponding amines under ambient conditions

Ist Teil von

• Tetrahedron letters, 2017-10, Vol.58 (43), p.4073-4077

Ort / Verlag

Elsevier Ltd

Erscheinungsjahr

2017

Link zum Volltext

Quelle

Elsevier ScienceDirect Journals Complete

Beschreibungen/Notizen

• [Display omitted] •Development of reducing agent diisobutylaluminum borohydride.•Tertiary amides reduced to the corresponding amine under ambient conditions.•No column purification technique required for isolation of amine product. A synthetically simple mixed metal hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], is easily generated from a 1:1 mixture of borane-dimethylsulfide (BMS) and diisobutylaluminum hydride (DIBAL). The reduction of tertiary amides using (iBu)2AlBH4 is complete within five minutes under ambient conditions and the product tertiary amines were isolated in 70–99% yields by a simple acid-base extraction. This new methodology, reported herein, works well for reduction of tertiary aliphatic and aromatic amides as well as lactams to the corresponding amines and product isolation and purification does not require column chromatography.