Metal-Free -C(sp(3))-H Functionalized Oxidative Cyclization of Tertiary N,N-Diarylamino Alcohols: Construction of N,N-Diarylaminotetrahydropyran Scaffolds

Herein, we report an efficient synthetic method for the preparation of anomeric N,N-diarylaminotetrahydropyran scaffolds. The free radical 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)/hypervalent iodine(III)- or TEMPO/I-2-mediated oxidative cyclization of tertiary amino alcohols was used to construc...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 5; no. 2; pp. 232 - 239
Main Authors Afzal, Sualiha, Venkanna, Arramshetti, Park, Hyeung-geun, Kim, Mi-hyun
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.02.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
tertiary amines
MECHANISM
SCOPE
6-exo-trig
metal-free reactions
QUINOLINES
IODINE
oxidative cyclization
DIRECTING-GROUP
C-H ACTIVATION
C(sp)-H functionalization
AMINES
NITROGEN ATOM
BONDS
DERIVATIVES
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Summary:Herein, we report an efficient synthetic method for the preparation of anomeric N,N-diarylaminotetrahydropyran scaffolds. The free radical 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)/hypervalent iodine(III)- or TEMPO/I-2-mediated oxidative cyclization of tertiary amino alcohols was used to construct N,N-diarylaminotetrahydropyrans through -C(sp(3))-O bond formation, with the loss of only two Hatoms. This efficient synthetic method broadens the scope of viable -C(sp(3))-H functionalized amines to include conformational-bias-free substrates.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201500392