Intermolecular Radical Mediated Anti-Markovnikov Alkene Hydroamination Using N-Hydroxyphthalimide | Zendy

Samuel W. Lardy | Zendy; Valerie A. Schmidt | Zendy

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Intermolecular Radical Mediated Anti-Markovnikov Alkene Hydroamination Using N-Hydroxyphthalimide

Author(s) -

Samuel W. Lardy,

Valerie A. Schmidt

Publication year - 2018

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.8b06881

Subject(s) - markovnikov's rule , chemistry , hydroamination , alkene , radical , intermolecular force , silanes , organic chemistry , deoxygenation , primary (astronomy) , hydrosilylation , combinatorial chemistry , photochemistry , catalysis , regioselectivity , molecule , silane , physics , astronomy

An intermolecular anti-Markovnikov hydroamination of alkenes has been developed using triethyl phosphite and N-hydroxyphthalimide. The process tolerates a wide range of alkenes, including vinyl ethers, silanes, and sulfides as well as electronically unbiased terminal and internal alkenes. The resultant N-alkylphthalimides can readily be transformed to the corresponding primary amines. Mechanistic probes indicate that the process is mediated via a phosphite promoted radical deoxygenation of N-hydroxyphthalimide to access phthalimidyl radicals.

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