Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes

被引：23

作者：

Rao, H. Surya Prakash ^{[1
]}

Rao, A. Veera Bhadra ^{[1
]}

机构：

[1] Pondicherry Univ, Dept Chem, Pondicherry 605014, India

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 12卷

关键词：

copper; modular synthesis; triarylmethanes; CROSS-COUPLING REACTIONS; AROMATIC-ALDEHYDES; TRIETHYL ORTHOFORMATE; STRUCTURE ELUCIDATION; REDUCTASE INHIBITORS; ANTIVIRAL ACTIVITIES; BENZYLIC ALCOHOLS; RATIONAL DESIGN; CUPRIC ACETATE; ARYL HALIDES;

D O I：

10.3762/bjoc.12.49

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and modular synthesis of triarylmethanes was achieved in good yield via a two-step sequence in which the final step is the copper(II)-catalyzed arylation of diarylmethanols with arylboronic acids. By using this protocol a variety of symmetrical and unsymmetrical triarylmethanes were synthesized. As an application of the newly developed methodology, we demonstrate a high-yielding synthesis of the triarylmethane intermediate towards an anti-breast-cancer drug candidate.

引用

页码：496 / 504

页数：9

共 50 条

[41] Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki Coupling of Trimethylammonium Salts and Arylboronic Acids
Zhang, Zhenming
Wang, Hui
Qiu, Nianli
Kong, Yujing
Zeng, Wenjuan
Zhang, Yongquan
Zhao, Junfeng
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15): : 8710 - 8715
[42] Synthesis of 2,5-diaryloxazoles through van Leusen reaction and copper-mediated direct arylation
Yoshizumi, Tomoki
Satoh, Tetsuya
Hirano, Koji
Matsuo, Daisuke
Orita, Akihiro
Otera, Junzo
Miura, Masahiro
[J]. TETRAHEDRON LETTERS, 2009, 50 (26) : 3273 - 3276
[43] Synthesis of symmetrical diaryl ethers from arylboronic acids mediated by copper(II) acetate
Sagar, AD
Tale, RH
Adude, RN
[J]. TETRAHEDRON LETTERS, 2003, 44 (37) : 7061 - 7063
[44] Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone
Nambo, Masakazu
Crudden, Cathleen M.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (03) : 742 - 746
[45] Copper-Mediated Radiocyanation of Unprotected Amino Acids and Peptides
Sharninghausen, Liam S.
Preshlock, Sean
Joy, Stephen T.
Horikawa, Mami
Shao, Xia
Winton, Wade P.
Stauff, Jenelle
Kaur, Tanpreet
Koeppe, Robert A.
Mapp, Anna K.
Scott, Peter J. H.
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (16) : 7422 - 7429
[46] Copper-mediated N- and O-arylations with arylboronic acids in a continuous flow microreactor: a new avenue for efficient scalability
Singh, Brajendra K.
Stevens, Christian V.
Acke, Davy R. J.
Parmar, Virinder S.
Van der Eycken, Erik V.
[J]. TETRAHEDRON LETTERS, 2009, 50 (01) : 15 - 18
[47] Copper-mediated N-arylation of electron-deficient pyrroles and indoles
Bekolo, Henri
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2007, 85 (01): : 42 - 46
[48] Site-Selective, Copper-Mediated O-Arylation of Carbohydrate Derivatives
Dimakos, Victoria
Garrett, Graham E.
Taylor, Mark S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (43) : 15515 - 15521
[49] Total Synthesis of (-)-Melanthioidine by Copper-Mediated Cyclodimerization
Wang, Jianjun
Evano, Gwilherm
[J]. ORGANIC LETTERS, 2016, 18 (15) : 3542 - 3545
[50] Ligand-free copper-mediated N-arylation of spirocyclic lactams
Yang, Wei
Coutinho, Ana Luisa
Abdel-Hafez, Atef A.
Jiang, Chao
Xue, Fengtian
[J]. TETRAHEDRON LETTERS, 2015, 56 (41) : 5599 - 5603

← 1 2 3 4 5 →