Diborane-Mediated Deoxygenation of o-Nitrostyrenes To Form Indoles | Zendy

Kai Yang | Zendy; Fei Zhou | Zendy; Zhijie Kuang | Zendy; Guoliang Gao | Zendy; Tom G. Driver | Zendy; Qiuling Song | Zendy

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Diborane-Mediated Deoxygenation of o-Nitrostyrenes To Form Indoles

Author(s) -

Kai Yang,

Fei Zhou,

Zhijie Kuang,

Guoliang Gao,

Tom G. Driver,

Qiuling Song

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b01934

Subject(s) - deoxygenation , chemistry , diborane , reactivity (psychology) , nitro , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , boron , medicine , alkyl , alternative medicine , pathology

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 σpara values. Our new deoxygenation reaction is efficient, practical, and scaleable, enabling access to a broad range of indoles.

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