Nickel-Catalyzed [4+2] Annulation of Nitriles and Benzylamines by C-H/N-H Activation

被引：23

作者：

Sikari, Rina ^{[1
]}

Chakraborty, Gargi ^{[1
]}

Guin, Amit Kumar ^{[1
]}

Paul, Nanda D. ^{[1
]}

机构：

[1] Indian Inst Engn Sci & Technol, Dept Chem, Howrah 711103, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 01期

关键词：

2-SUBSTITUTED QUINAZOLINES; C(SP(3))-H BONDS; FUNCTIONALIZATION; ALKYLATION; ARYLATION; AMIDES; ALKENYLATION; COMPLEXES; OXIDATION; STRATEGY;

D O I：

10.1021/acs.joc.0c02069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nickel-catalyzed [4 + 2] annulation of benzylamines and nitriles via C-H/N-H bond activation, providing straightforward atom-economic access to a wide variety of multisubstituted quinazolines, is reported. Mechanistic investigation revealed that the in situ formed amidines from the coupling of benzylamines and nitriles direct the nickel catalyst to activate the ortho-C-H bond of the phenyl ring of the benzylamine.

引用

页码：279 / 290

页数：12

共 50 条

[41] Electricity Induced Rhodium-Catalyzed Oxidative C-H/N-H Annulation of Alkynes with Arylhydrophthalazinediones
Sen, Partha Pratim
Prakash, Rashmi
Roy, Sudipta Raha
ORGANIC LETTERS, 2022, : 4530 - 4535
[42] Ruthenium(ii)-catalyzed C-H activation and (4+2) annulation of aromatic hydroxamic acid esters with allylic amides
Giri, Chandan Kumar
Dana, Suman
Baidya, Mahiuddin
CHEMICAL COMMUNICATIONS, 2021, 57 (81) : 10536 - 10539
[43] Nickel-catalyzed N-vinylation of heteroaromatic amines via C-H bond activation
Landge, Vinod G.
Rana, Jagannath
Subaramanian, Murugan
Balaraman, Ekambaram
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (33) : 6896 - 6900
[44] Cobalt(III)-Catalyzed Synthesis of Fused Quinazolinones by C-H/N-H Annulation of 2-Arylquinazolinones with Alkynes
Kumaran, Subramani
Parthasarathy, Kanniyappan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (07) : 866 - 869
[45] Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C-H Activation/Alkyne Insertion Reaction
Castro, Luis C. Misal
Obata, Atsushi
Aihara, Yoshinori
Chatani, Naoto
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (04) : 1362 - 1367
[46] Nickel-Catalyzed C-F/N-H Annulation of Aromatic Amides with Alkynes: Activation of C-F Bonds under Mild Reaction Conditions
Nohira, Itsuki
Liu, Song
Bai, Ruopeng
Lan, Yu
Chatani, Naoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (41) : 17306 - 17311
[47] Nickel-Catalyzed C-F/N-H Annulation of Aromatic Amides with Alkynes: Activation of C-F Bonds under Mild Reaction Conditions
Nohira, Itsuki
Liu, Song
Bai, Ruopeng
Lan, Yu
Chatani, Naoto
Journal of the American Chemical Society, 2020, 142 (41): : 17306 - 17311
[48] Rh-Catalyzed [4+2] Annulation with a Removable Monodentate Structure toward Iminopyranes and Pyranones by C-H Annulation
Fu, Leiqing
Xu, Wenqiang
Pu, Maoping
Wu, Yun-Dong
Liu, Yunyun
Wan, Jie-Ping
ORGANIC LETTERS, 2022, 24 (16) : 3003 - 3008
[49] Nickel-Catalyzed C-H Heteroarylation of Chiral Oxazolines
Lu, Peng
Ji, Chong-Lei
Lu, Zhan
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (03) : 542 - 544
[50] Photoredox catalysis in nickel-catalyzed C-H functionalization
Mantry, Lusina
Maayuri, Rajaram
Kumar, Vikash
Gandeepan, Parthasarathy
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 2209 - 2259

← 1 2 3 4 5 →