Literature DB >> 25062493

Acetic acid promoted metal-free aerobic carbon-carbon bond forming reactions at α-position of tertiary amines.

Hirofumi Ueda1, Kei Yoshida, Hidetoshi Tokuyama.   

Abstract

The oxidative functionalization of the benzylic C-H bonds in tetrahydroisoquinolines and tetrahydro-β-carboline derivatives was investigated. C-C bond forming reactions proceeded with a range of nucleophiles (nitroalkane, enol silyl ether, indole, allylstannane, and tetrabutylammonium cyanide) under metal-free conditions and an oxygen atmosphere. Acetic acid caused a significant acceleration effect.

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Year:  2014        PMID： 25062493     DOI： 10.1021/ol5018883

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  Metal-free C(sp(3))-H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization.

Authors:  Nan-Nan Wang; Wen-Juan Hao; Tian-Shu Zhang; Guigen Li; Ya-Nan Wu; Shu-Jiang Tu; Bo Jiang
Journal:  Chem Commun (Camb)       Date:  2016-03-21       Impact factor: 6.222

2.  Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?

Authors:  Alexander V Aksenov; Nicolai A Aksenov; Nikita K Kirilov; Anton A Skomorokhov; Dmitrii A Aksenov; Igor A Kurenkov; Elena A Sorokina; Mezvah A Nobi; Michael Rubin
Journal:  RSC Adv       Date:  2021-11-04       Impact factor: 4.036

3.  Toward Rational Understandings of α-C-H Functionalization: Energetic Studies of Representative Tertiary Amines.

Authors:  Wenzhi Luo; Jin-Dong Yang; Jin-Pei Cheng
Journal:  iScience       Date:  2020-01-21

4.  Oxidative cyanation of N-aryltetrahydroisoquinoline induced by visible light for the synthesis of α-aminonitrile using potassium thiocyanate as a "CN" agent.

Authors:  Bing Yi; Ning Yan; Niannian Yi; Yanjun Xie; Xiaoyong Wen; Chak-Tong Au; Donghui Lan
Journal:  RSC Adv       Date:  2019-09-19       Impact factor: 4.036

5.  Direct intramolecular double cross-dehydrogentive-coupling (CDC) cyclization of N-(2-pyridyl)amidines under metal-free conditions.

Authors:  Fengping Yi; Chao Fu; Qihui Sun; Huazhen Wei; Genfa Yu; Weiyin Yi
Journal:  RSC Adv       Date:  2019-12-19       Impact factor: 3.361
  5 in total

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