Literature DB >> 22984300

o-(Trialkylstannyl)anilines and Their Utility in Stille Cross-Coupling: Direct Introduction of the 2-Aminophenyl Substituent.

Enver Cagri Izgu1, Thomas R Hoye.   

Abstract

We have developed shelf- and air-stable ortho-stannylated aniline reagents that can directly be coupled with alkenyl and aryl halides via Stille cross-coupling. We report i) the efficient preparation of o-(tributylstannyl)aniline (2a) and o-(trimethylstannyl)aniline (2b), ii) the comparison of the reactivities of 2a and 2b with those of related organostannanes in cross-coupling reaction with an alkenyl halide, and iii) the cross-coupling of 2a and 2b with a series of arylhalides and triflate.

Entities:  

Year:  2012        PMID: 22984300      PMCID: PMC3439219          DOI: 10.1016/j.tetlet.2012.06.138

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  9 in total

1.  Total synthesis of (+/-)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi.

Authors:  Martin G Banwell; Alison J Edwards; Katrina A Jolliffe; Jason A Smith; Ernest Hamel; Pascal Verdier-Pinard
Journal:  Org Biomol Chem       Date:  2003-01-21       Impact factor: 3.876

2.  Stille coupling made easier-the synergic effect of copper(I) salts and the fluoride ion.

Authors:  Simon P H Mee; Victor Lee; Jack E Baldwin
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-20       Impact factor: 15.336

3.  Rational design of novel, potent small molecule pan-selectin antagonists.

Authors:  Remo Kranich; Anke S Busemann; Daniel Bock; Sabine Schroeter-Maas; Diana Beyer; Bo Heinemann; Michael Meyer; Katrin Schierhorn; Rainer Zahlten; Gerhard Wolff; Ewald M Aydt
Journal:  J Med Chem       Date:  2007-02-16       Impact factor: 7.446

4.  Biphenylsulfonamide endothelin antagonists: structure-activity relationships of a series of mono- and disubstituted analogues and pharmacology of the orally active endothelin antagonist 2'-amino-N- (3,4-dimethyl-5-isoxazolyl)-4'-(2-methylpropyl)[1, 1'-biphenyl]-2-sulfonamide (BMS-187308).

Authors:  N Murugesan; Z Gu; P D Stein; S Bisaha; S Spergel; R Girotra; V G Lee; J Lloyd; R N Misra; J Schmidt; A Mathur; L Stratton; Y F Kelly; E Bird; T Waldron; E C Liu; R Zhang; H Lee; R Serafino; B Abboa-Offei; P Mathers; M Giancarli; A A Seymour; M L Webb; J T Hunt
Journal:  J Med Chem       Date:  1998-12-17       Impact factor: 7.446

5.  Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams.

Authors:  Olivier Baudoin; Michèle Cesario; Daniel Guénard; Françoise Guéritte
Journal:  J Org Chem       Date:  2002-02-22       Impact factor: 4.354

6.  Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2'-disubstituted biphenyls.

Authors:  O Baudoin; D Guénard; F Guéritte
Journal:  J Org Chem       Date:  2000-12-29       Impact factor: 4.354

7.  NiCl2(PMe3)(2)-catalyzed borylation of aryl chlorides.

Authors:  Tetsuya Yamamoto; Tomoyuki Morita; Jun Takagi; Tetsu Yamakawa
Journal:  Org Lett       Date:  2011-10-06       Impact factor: 6.005

8.  Six-step synthesis of (S)-brevicolline from (S)-nicotine.

Authors:  Florence F Wagner; Daniel L Comins
Journal:  Org Lett       Date:  2006-08-03       Impact factor: 6.005

9.  Stereoselective synthesis of the epicoccin core.

Authors:  Ulrike Gross; Martin Nieger; Stefan Bräse
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

  9 in total
  2 in total

1.  Total synthesis of (±)-leuconolam: intramolecular allylic silane addition to a maleimide carbonyl group.

Authors:  Enver Cagri Izgu; Thomas R Hoye
Journal:  Chem Sci       Date:  2013-02       Impact factor: 9.825

2.  4-alkyl-L-(Dehydro)proline biosynthesis in actinobacteria involves N-terminal nucleophile-hydrolase activity of γ-glutamyltranspeptidase homolog for C-C bond cleavage.

Authors:  Guannan Zhong; Qunfei Zhao; Qinglin Zhang; Wen Liu
Journal:  Nat Commun       Date:  2017-07-14       Impact factor: 14.919

  2 in total

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