Literature DB >> 22313416

Me3(OMe)tBuXPhos: a surrogate ligand for Me4tBuXPhos in palladium-catalyzed C-N and C-O bond-forming reactions.

Satoshi Ueda1, Siraj Ali, Brett P Fors, Stephen L Buchwald.   

Abstract

A new biarylphosphine ligand, Me(3)(OMe)tBuXPhos (L3), was designed as a surrogate for Me(4)tBuXPhos (L1). The Me(3)(OMe)tBuXPhos could be prepared in a chromatography-free manner from inexpensive and readily available 2,3,6-trimethylphenol. Comparative studies demonstrated that a catalyst based on Me(3)(OMe)tBuXPhos displayed the same reactivity as a catalyst based on Me(4)tBuXPhos for Pd-catalyzed C-N and C-O bond-forming processes.

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Year:  2012        PMID： 22313416      PMCID： PMC3387921          DOI： 10.1021/jo202537e

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  11 in total

1.  Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles.

Authors:  Kevin W Anderson; Rachel E Tundel; Takashi Ikawa; Ryan A Altman; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2006-10-06       Impact factor: 15.336

2.  General and modular synthesis of isomeric 5-substituted pyridin-2-yl and 6-substituted pyridin-3-yl C-ribonucleosides bearing diverse alkyl, aryl, hetaryl, amino, carbamoyl, and hydroxy groups.

Authors:  Martin Štefko; Lenka Slavětínská; Blanka Klepetářová; Michal Hocek
Journal:  J Org Chem       Date:  2011-07-25       Impact factor: 4.354

3.  The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans.

Authors:  Kevin W Anderson; Takashi Ikawa; Rachel E Tundel; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2006-08-23       Impact factor: 15.419

4.  Synthesis of fused carbocycles via a selective 6-endo dig gold(I)-catalyzed carbocyclization.

Authors:  Francis Barabé; Patrick Levesque; Ilia Korobkov; Louis Barriault
Journal:  Org Lett       Date:  2011-09-15       Impact factor: 6.005

5.  Highly N2-selective palladium-catalyzed arylation of 1,2,3-triazoles.

Authors:  Satoshi Ueda; Mingjuan Su; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-18       Impact factor: 15.336

6.  A general and efficient synthesis of pyridin-2-yl C-ribonucleosides bearing diverse alkyl, aryl, amino, and carbamoyl groups in position 6.

Authors:  Martin Stefko; Lenka Slavetínská; Blanka Klepetárová; Michal Hocek
Journal:  J Org Chem       Date:  2010-01-15       Impact factor: 4.354

7.  Water-mediated catalyst preactivation: an efficient protocol for C-N cross-coupling reactions.

Authors:  Brett P Fors; Philipp Krattiger; Eric Strieter; Stephen L Buchwald
Journal:  Org Lett       Date:  2008-07-12       Impact factor: 6.005

8.  Pd-catalyzed amidation of aryl chlorides using monodentate biaryl phosphine ligands: a kinetic, computational, and synthetic investigation.

Authors:  Takashi Ikawa; Timothy E Barder; Mark R Biscoe; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

9.  Synthetic approaches to the microtubule-stabilizing sponge alkaloid ceratamine A and desbromo analogues.

Authors:  Matt Nodwell; Alban Pereira; Jenna L Riffell; Carla Zimmerman; Brian O Patrick; Michel Roberge; Raymond J Andersen
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

10.  Completely N1-selective palladium-catalyzed arylation of unsymmetric imidazoles: application to the synthesis of nilotinib.

Authors:  Satoshi Ueda; Mingjuan Su; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2011-12-14       Impact factor: 15.419
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  5 in total

1.  Structure-Based Discovery of 4-(6-Methoxy-2-methyl-4-(quinolin-4-yl)-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole (CD161) as a Potent and Orally Bioavailable BET Bromodomain Inhibitor.

Authors:  Yujun Zhao; Longchuan Bai; Liu Liu; Donna McEachern; Jeanne A Stuckey; Jennifer L Meagher; Chao-Yie Yang; Xu Ran; Bing Zhou; Yang Hu; Xiaoqin Li; Bo Wen; Ting Zhao; Siwei Li; Duxin Sun; Shaomeng Wang
Journal:  J Med Chem       Date:  2017-05-02       Impact factor: 7.446

2.  Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF3 as an Additive.

Authors:  Yuxuan Ye; Takashi Takada; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-15       Impact factor: 15.336

3.  Optimization of 3-Pyrimidin-4-yl-oxazolidin-2-ones as Orally Bioavailable and Brain Penetrant Mutant IDH1 Inhibitors.

Authors:  Qian Zhao; James R Manning; James Sutton; Abran Costales; Martin Sendzik; Cynthia M Shafer; Julian R Levell; Gang Liu; Thomas Caferro; Young Shin Cho; Mark Palermo; Gregg Chenail; Julia Dooley; Brian Villalba; Ali Farsidjani; Jinyun Chen; Stephanie Dodd; Ty Gould; Guiqing Liang; Kelly Slocum; Minying Pu; Brant Firestone; Joseph Growney; Tycho Heimbach; Raymond Pagliarini
Journal:  ACS Med Chem Lett       Date:  2018-06-11       Impact factor: 4.345

4.  Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts.

Authors:  Chi Wai Cheung; David S Surry; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-07-01       Impact factor: 6.005

5.  Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.

Authors:  Bryan T Ingoglia; Corin C Wagen; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2019-05-11       Impact factor: 2.457
  5 in total

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