Synthesis of Tetraarylmethanes by the Triflic Acid-Promoted Formal Cross-Dehydrogenative Coupling of Triarylmethanes with Arenes

被引：17

作者：

Nambo, Masakazu ^{[1
]}

Yim, Jacky C. -H. ^{[1
]}

Fowler, Kevin G. ^{[1
]}

Crudden, Cathleen M. ^{[1
,2
]}

机构：

[1] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan

[2] Queens Univ, Dept Chem, Chernoff Hall, Kingston, ON K7L 3N6, Canada

来源：

SYNLETT | 2017年 / 28卷 / 20期

关键词：

cross-coupling; dehydrogenation; tetraarylmethanes; triarylmethanes; arylation; organocatalysis; CATALYZED SEQUENTIAL ARYLATION; SCHOLL REACTION; HALIDES; CATION; BOND; ALKYLATION; AROMATICS; EFFICIENT; SULFONE; CDC;

D O I：

10.1055/s-0036-1588563

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The formal cross-dehydrogenative coupling of triarylmethanes with arenes promoted by triflic acid and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone is described. This method provides a variety of tetraarylmethane derivatives in good to excellent yields from triarylmethanes that can be readily prepared by our previous methods. Control experiments suggest a possible catalytic cycle involving the generation of a trityl cation intermediate followed by nucleophilic addition of the arene.

引用

页码：2936 / 2940

页数：5

共 50 条

[31] Frontiers in Copper-promoted C1-functionalization of Tetrahydroisoquinoline using Cross-dehydrogenative Coupling
Upadhyay, Rachana
Patel, Amit B.
CURRENT ORGANIC CHEMISTRY, 2023, 27 (14) : 1255 - 1276
[32] Cs2CO3-promoted cross-dehydrogenative coupling of thiophenols with active methylene compounds
Chen, Qian
Wang, Xiaofeng
Wen, Chunxiao
Huang, Yulin
Yan, Xinxing
Zeng, Jiekun
RSC ADVANCES, 2017, 7 (63): : 39758 - 39761
[33] KBrO3-Promoted Cross-Dehydrogenative Coupling Reaction: An Odorless Regioselective Sulfenylation of Imidazoheterocycles in Water
Cui, Xiao-lin
Tian, Hao-yu
Wang, Shuo-jin
Chen, Xun
Kong, Du-lin
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 8576 - 8582
[34] Visible-Light-Promoted Direct Amination of Phenols via Oxidative Cross-Dehydrogenative Coupling Reaction
Zhao, Yating
Huang, Binbin
Yang, Chao
Xia, Wujiong
ORGANIC LETTERS, 2016, 18 (14) : 3326 - 3329
[35] TRIFLIC ACID-PROMOTED REGIO AND STEREOSELECTIVE SYNTHESIS OF POLYFUNCTIONALIZED ENAMINONES FROM DIBENZYLIDENE KETONES AND ORGANIC AZIDES
Prates, Lucas Souza
Cunha, Silvio
QUIMICA NOVA, 2025, 48 (04):
[36] Palladium-catalyzed synthesis of indole fused coumarins via cross-dehydrogenative coupling
Dey, Amrita
Ali, Md Ashif
Jana, Sourav
Samanta, Sadhanendu
Hajra, Alakananda
TETRAHEDRON LETTERS, 2017, 58 (04) : 313 - 316
[37] Synthesis of Dihydroindoloisoquinolines through Copper-Catalyzed Cross-Dehydrogenative Coupling of Tetrahydroisoquinolines and Nitroalkanes
Martin-Garcia, Iris
Alonso, Francisco
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (71) : 18857 - 18862
[38] Synthesis of Heteroatom-Containing Organic Molecules via Intramolecular Cross-Dehydrogenative Coupling
Batra, Aanchal
Kaur, Manjot
Singh, Pushpinder
Singh, Kamal Nain
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
[39] Synthesis of α-Substituted Primary Benzylamines through Copper-Catalyzed Cross-Dehydrogenative Coupling
Kramer, Soren
ORGANIC LETTERS, 2019, 21 (01) : 65 - 69
[40] Pd(<sc>ii</sc>) NCSe-pincer complexes for regioselective cross-dehydrogenative coupling of arylthiophenes with hetero(arenes)
Singh, Sohan
Mahala, Suman
Bhuvanesh, Nattamai
Joshi, Hemant
CATALYSIS SCIENCE & TECHNOLOGY, 2025, 15 (02) : 523 - 536

← 1 2 3 4 5 →