Diborane-Mediated Deoxygenation of o-Nitrostyrenes To Form Indoles

详细信息    查看全文

• 作者：Kai Yang ; Fei Zhou ; Zhijie Kuang ; Guoliang Gao ; Tom G. Driver ; Qiuling Song
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：August 19, 2016
• 年：2016
• 卷：18
• 期：16
• 页码：4088-4091
• 全文大小：401K
• 年卷期：0
• ISSN：1523-7052

文摘

A mild, transition metal-free, diborane-mediated deoxygenation of nitro groups was discovered that in situ generates nitrosoarene reactive intermediates. This new reactivity mode of B₂pin₂ was leveraged to construct indoles from o-nitrostyrenes through a reductive-cyclization reaction that exhibits a Hammett ρ-value of +0.97 relative to σ_para values. Our new deoxygenation reaction is efficient, practical, and scaleable, enabling access to a broad range of indoles.