Deoxygenative cross-coupling of aryl ketones with (Hetero)arenes mediated by a TiCl4/Ammonia borane system

被引：0

作者：

Zang, Yong-jun ^{[1
]}

Zhou, Shi-jie ^{[1
]}

Qian, Chen ^{[1
]}

Xu, Qi-lin ^{[1
]}

Li, Guo-si ^{[1
]}

Li, Xing ^{[2
]}

Zhu, Fu-cheng ^{[1
]}

机构：

[1] West Anhui Univ, Dept Biol & Pharmaceut Engn, Anhui Prov Key Lab Qual Evaluat & Improvement Trad, Luan 237012, Anhui, Peoples R China

[2] Taizhou Univ, Lege Pharm & Chem & Chem Engn, Taizhou 225300, Jiangsu, Peoples R China

来源：

TETRAHEDRON | 2024年 / 163卷

基金：

中国国家自然科学基金;

关键词：

Deoxygenative coupling; Aromatic ketones; Ammonia borane; Titanium tetrachloride; FRIEDEL-CRAFTS ALKYLATION; REDUCTIVE ALKYLATION; ARENES; TRIARYLMETHANES; INDOLES;

D O I：

10.1016/j.tet.2024.134147

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and mild protocol for the direct deoxygenative coupling of aryl ketones with electron-rich (hetero) arenes to construct the C(sp2)- 2 )- C(sp3) 3 ) bond was achieved, which was mediated by TiCl4 4 and by using ammonia borane (AB) as the reductant. This strategy provides a novel protocol for the synthesis of unsymmetrical diaryland triarylmethanes.

引用

页数：6

共 26 条

[1] Cascade Reductive Friedel-Crafts Alkylation Catalyzed by Robust Iridium(III) Hydride Complexes Containing a Protic Triazolylidene Ligand [J].

Alshakova, Iryna D. ;

Albrecht, Martin .

ACS CATALYSIS, 2021, 11 (15) :8999-9007

[2] C(sp3)-C(sp3) bond formation via nickel-catalyzed deoxygenative homo-coupling of aldehydes/ketones mediated by hydrazine [J].

Cao, Dawei ;

Li, Chen-Chen ;

Zeng, Huiying ;

Peng, Yong ;

Li, Chao-Jun .

NATURE COMMUNICATIONS, 2021, 12 (01)

[3] Molecular Iodine-Catalysed Reductive Alkylation of Indoles: Late-Stage Diversification for Bioactive Molecules [J].

Cheng, Xionglve ;

Wang, Lili ;

Liu, Yide ;

Wan, Xiao ;

Xiang, Zixin ;

Li, Ruyi ;

Wan, Xiaobing .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (34)

[4] Superacid-catalyzed reductive Friedel-Crafts reaction of arenes using arenecarbaldehyde acetals [J].

Fukuzawa, S ;

Tsuchimoto, T ;

Hiyama, T .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (01) :151-156

[5] Ruthenium(ii)-catalyzed deoxygenation of ketones [J].

Gui, Ruohua ;

Li, Chao-Jun .

CHEMICAL COMMUNICATIONS, 2022, 58 (75) :10572-10575

[6] GALLIUM DICHLORIDE-MEDIATED REDUCTIVE FRIEDEL-CRAFTS REACTION [J].

HASHIMOTO, Y ;

HIRATA, K ;

KAGOSHIMA, H ;

KIHARA, N ;

HASEGAWA, M ;

SAIGO, K .

TETRAHEDRON, 1993, 49 (27) :5969-5978

[7] Triflic Acid/Silane Promoted Deoxygenative Transformation of Ketones via Carbocations [J].

Hou, Jianxin ;

Han, Xue ;

Zhang, Yiyi ;

Huang, Jiahui ;

Wang, Jiawei ;

Yuan, Kedong .

ORGANIC LETTERS, 2023, 25 (31) :5709-5713

[8] Iodine catalyzed Friedel-Crafts alkylation of electron-rich arenes with aldehydes: efficient synthesis of triarylmethanes and diarylalkanes [J].

Jaratjaroonphong, Jaray ;

Sathalalai, Supaporn ;

Techasauvapak, Prapapan ;

Reutrakul, Vichai .

TETRAHEDRON LETTERS, 2009, 50 (44) :6012-6015

[9] Advances in The Catalytic Synthesis of Triarylmethanes (TRAMs) [J].

Kshatriya, Rajpratap ;

Jejurkar, Valmik P. ;

Saha, Satyajit .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (24) :3818-3841

[10] Deoxygenative Functionalizations of Aldehydes, Ketones and Carboxylic Acids [J].

Li, Jianbin ;

Huang, Chia-Yu ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (10)

← 1 2 3 →