Literature DB >> 24307286

Modular synthesis of triarylmethanes through palladium-catalyzed sequential arylation of methyl phenyl sulfone.

Masakazu Nambo1, Cathleen M Crudden.   

Abstract

Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane-based materials and pharmaceuticals.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; N-heterocyclic carbenes; Suzuki-Miyaura coupling; palladium; sulfones

Mesh:

Substances:

Year:  2013        PMID: 24307286     DOI: 10.1002/anie.201307019

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  12 in total

1.  Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.

Authors:  Bing Zheng; Minyan Li; Gui Gao; Yuying He; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2016-06-15       Impact factor: 5.837

2.  Selective synthesis of either enantiomer of an anti-breast cancer agent via a common enantioenriched intermediate.

Authors:  Aaron George Johnson; Marissa M Tranquilli; Michael R Harris; Elizabeth R Jarvo
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters.

Authors:  Amira H Dardir; Irene Casademont-Reig; David Balcells; Jonathan D Ellefsen; Matthew R Espinosa; Nilay Hazari; Nicholas E Smith
Journal:  Organometallics       Date:  2021-05-27       Impact factor: 3.837

4.  Hydride Reduction by a Sodium Hydride-Iodide Composite.

Authors:  Pei Chui Too; Guo Hao Chan; Ya Lin Tnay; Hajime Hirao; Shunsuke Chiba
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-16       Impact factor: 15.336

5.  Light-induced metal-free transformations of unactivated pyridotriazoles.

Authors:  Ziyan Zhang; Dongari Yadagiri; Vladimir Gevorgyan
Journal:  Chem Sci       Date:  2019-07-25       Impact factor: 9.825

6.  TBAB-Catalyzed 1,6-Conjugate Sulfonylation of para-Quinone Methides: A Highly Efficient Approach to Unsymmetrical gem-Diarylmethyl Sulfones in Water.

Authors:  Zhang-Qin Liu; Peng-Sheng You; Liang-Dong Zhang; Da-Qing Liu; Sheng-Shu Liu; Xiao-Yu Guan
Journal:  Molecules       Date:  2020-01-26       Impact factor: 4.411

7.  Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents.

Authors:  Baosheng Wei; Qianyi Ren; Thomas Bein; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-17       Impact factor: 15.336

8.  Nickel-Catalyzed Arylation of Heteroaryl-containing Diarylmethanes: Exceptional Reactivity of the Ni(NIXANTPHOS)-based Catalyst.

Authors:  Xinyu Cao; Sheng-Chun Sha; Minyan Li; Byeong-Seon Kim; Catherine Morgan; Rudan Huang; Xiaodong Yang; Patrick J Walsh
Journal:  Chem Sci       Date:  2015-10-26       Impact factor: 9.825

Review 9.  Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry.

Authors:  Ugo Azzena; Massimo Carraro; Luisa Pisano; Serena Monticelli; Roberta Bartolotta; Vittorio Pace
Journal:  ChemSusChem       Date:  2018-11-20       Impact factor: 8.928

10.  Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling.

Authors:  Masakazu Nambo; Jacky C-H Yim; Luiza B O Freitas; Yasuyo Tahara; Zachary T Ariki; Yuuki Maekawa; Daisuke Yokogawa; Cathleen M Crudden
Journal:  Nat Commun       Date:  2019-10-04       Impact factor: 14.919

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