Light‐Mediated Deoxygenation of Alcohols with a Dimeric Gold Catalyst. Issue 1 (12th November 2014)

• Record Type: Journal Article
• Authors: McCallum, Terry; Slavko, Ekaterina; Morin, Mathieu; Barriault, Louis
• Is Part Of: European journal of organic chemistry. Issue 1(2015)
• Page Start: 81
• Page End: 85
• Publication Date: 2014-11-12
• Subjects: Radical reactions -- Photoredox catalysis -- Gold -- Deoxygenation -- Bromination; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403351
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A new protocol for the reductive deoxygenation of primary alcohols was explored. This photomediated method combines a novel approach to bromination of alcohols merged with the powerful reducing capability of [Au2 (dppm)2 ]Cl2 [dppm = 1, 1‐bis(diphenylphosphino)methane] as a photoredox catalyst. The highly efficient methods discussed are marked by the use of UVA light‐emitting diodes, which have significantly reduced reaction times and lowered setup cost. Abstract : While exploring orthogonal reactivity with [Au2 (dppm)2 ]Cl2 [dppm = 1, 1‐bis(diphenylphosphino)methane], the high‐yielding photochemical bromination of alcohols was found. The simplicity of this reaction makes it a perfect match for combining bromination with reductive dehalogenation through photoredox catalysis. The highly efficient one‐pot reductive deoxygenation protocol for primary alcohols is presented.