Visible-light-mediated, nitrogen-centered radical amination of tertiary alkyl halides under metal-free conditions to form α-tertiary amines

被引：27

作者：

Brueckner, Alexander C. ^{[1
]}

Hancock, Erin N. ^{[1
]}

Anders, Evan J. ^{[1
]}

Tierney, Matthew M. ^{[2
]}

Morgan, Heather R. ^{[2
]}

Scott, Kristina A. ^{[2
]}

Lamar, Angus A. ^{[2
]}

机构：

[1] Hanover Coll, Dept Chem, 484 Ball Dr, Hanover, IN 47243 USA

[2] Univ Tulsa, Dept Chem & Biochem, 800 South Tucker Dr, Tulsa, OK 74104 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 19期

关键词：

C-H AMINATION; AMIDATION; ALKENES; HYDROAMINATION; GENERATION; ARENES; HYDROCARBONS; PRECURSORS; IMIDATION; OXIDATION;

D O I：

10.1039/c6ob00616g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and operationally convenient amino-functionalization of a range of tertiary alkyl halides by reaction with iminoiodinanes (PhI=NNs) and I-2 has been developed. According to the mechanistic experiments described within, the reaction is speculated to proceed through a light-promoted, N-centered radical pathway involving a N,N-diiodosulfonamide reactive species. This method of direct N-incorporation offers an attractive alternative to the production of a-tertiary amines, a synthetically challenging structural class found in a variety of bioactive molecules.

引用

页码：4387 / 4392

页数：6

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