Literature DB >> 23061536

Chichibabin-type direct alkylation of pyridyl alcohols with alkyl lithium reagents.

Jenna L Jeffrey1, Richmond Sarpong.   

Abstract

Direct C(6) alkylation of pyridyl alcohols can be achieved following an initial deprotonation of the hydroxy group. This transformation, which is believed to occur by a Chichibabin-type alkylation, avoids lateral deprotonation prior to pyridine ring alkylation and gives increased regioselectivity for C(6) over C(4) alkylation.

Entities:  

Mesh:

Substances:

Year:  2012        PMID: 23061536      PMCID: PMC3503527          DOI: 10.1021/ol3024117

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


  20 in total

1.  Synthesis of versatile chiral N,P ligands derived from pyridine and quinoline.

Authors:  William J Drury; Nicole Zimmermann; Martine Keenan; Masahiko Hayashi; Stefan Kaiser; Richard Goddard; Andreas Pfaltz
Journal:  Angew Chem Int Ed Engl       Date:  2004-01       Impact factor: 15.336

2.  A new class of chiral P,N-ligands and their application in palladium-catalyzed asymmetric allylic substitution reactions.

Authors:  Michael P A Lyle; Arun A Narine; Peter D Wilson
Journal:  J Org Chem       Date:  2004-07-23       Impact factor: 4.354

Review 3.  Quinoline, quinazoline and acridone alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2005-08-24       Impact factor: 13.423

4.  Iridium catalysts with bicyclic pyridine-phosphinite ligands: asymmetric hydrogenation of olefins and furan derivatives.

Authors:  Stefan Kaiser; Sebastian P Smidt; Andreas Pfaltz
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-04       Impact factor: 15.336

5.  Design and synthesis of tridentate facially chelating ligands of the [2.n.1]-(2,6)-pyridinophane family.

Authors:  Andrei N Vedernikov; Maren Pink; Kenneth G Caulton
Journal:  J Org Chem       Date:  2003-06-13       Impact factor: 4.354

6.  The versatile, efficient, and stereoselective self-assembly of transition-metal helicates by using hydrogen-bonds.

Authors:  Shane G Telfer; Reiko Kuroda
Journal:  Chemistry       Date:  2004-12-17       Impact factor: 5.236

7.  Rare-earth-catalyzed C-H bond addition of pyridines to olefins.

Authors:  Bing-Tao Guan; Zhaomin Hou
Journal:  J Am Chem Soc       Date:  2011-10-20       Impact factor: 15.419

8.  Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

Authors:  Seung Hwan Cho; Seung Jun Hwang; Sukbok Chang
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

9.  Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine.

Authors:  Alexandre Larivée; James J Mousseau; André B Charette
Journal:  J Am Chem Soc       Date:  2007-12-08       Impact factor: 15.419

10.  Efficient chemoenzymatic synthesis of chiral pincer ligands.

Authors:  Fulvia Felluga; Walter Baratta; Lidia Fanfoni; Giuliana Pitacco; Pierluigi Rigo; Fabio Benedetti
Journal:  J Org Chem       Date:  2009-05-01       Impact factor: 4.354

View more
  5 in total

1.  Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters.

Authors:  Sébastien Laulhé; J Miles Blackburn; Jennifer L Roizen
Journal:  Chem Commun (Camb)       Date:  2017-06-29       Impact factor: 6.222

2.  Synthesis and Utility of Dihydropyridine Boronic Esters.

Authors:  Santanu Panda; Aaron Coffin; Q Nhu Nguyen; Dean J Tantillo; Joseph M Ready
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

3.  Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters.

Authors:  Sébastien Laulhé; J Miles Blackburn; Jennifer L Roizen
Journal:  Org Lett       Date:  2016-08-18       Impact factor: 6.005

4.  Reactivity of highly Lewis acidic diborane(4) towards pyridine and isocyanide: formation of boraalkene-pyridine complex and ortho-functionalized pyridine derivatives.

Authors:  Yuhei Katsuma; Hiroki Asakawa; Makoto Yamashita
Journal:  Chem Sci       Date:  2017-12-11       Impact factor: 9.825

5.  Organoborohydride-catalyzed Chichibabin-type C4-position alkylation of pyridines with alkenes assisted by organoboranes.

Authors:  Ying Wang; Runhan Li; Wei Guan; Yanfei Li; Xiaohong Li; Jianjun Yin; Ge Zhang; Qian Zhang; Tao Xiong; Qian Zhang
Journal:  Chem Sci       Date:  2020-09-29       Impact factor: 9.825

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.