Transition-Metal-Free Superbase-Catalyzed C-H Vinylation of Aldimines with Acetylenes to 1-Azadienes

被引：21

作者：

Schmidt, Elena Yu. ^{[1
]}

Bidusenko, Ivan A. ^{[1
]}

Protsuk, Nadezhda I. ^{[1
]}

Demyanov, Yan V. ^{[1
]}

Ushakov, Igor A. ^{[1
]}

Vashchenko, Alexander V. ^{[1
]}

Trofimov, Boris A. ^{[1
]}

机构：

[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 05期

基金：

俄罗斯科学基金会;

关键词：

ALPHA; BETA-UNSATURATED IMINES; SYNTHETIC APPLICATIONS; EFFICIENT SYNTHESIS; STEP ECONOMY; POT; ALDEHYDES; REDUCTION; KETONES; AMINES; ATOM;

D O I：

10.1021/acs.joc.9b03192

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldimines react with aryl- and hetarylacetylenes in the presence of KOBut/dimethyl sulfoxide (DMSO) or NaOBut/DMSO systems under exceptionally mild conditions (14 degrees C, 1 h) to afford C-H-vinylated products, 1-azadienes of E configuration relative to the C-C bond, in up to 72% yield. Vinylation involves the unprecedentedly fast multiposition proton transfer in the intermediate adducts of acetylene to the C=N bond. This new Csp(2)-Csp(2) bond-forming reaction opens a straightforward pot-, atom-, step-, and energy-economic access to synthetically valuable 1-azadienes.

引用

页码：3417 / 3425

页数：9

共 50 条

[1] Transition-Metal-Free C-H Alkylation of Cyclic Aldimines with Alkylboronic Acid
Zhou, Yu
Cui, Yangbo
Huang, Hangfei
Zhang, Jun-Qi
Xu, Yang
Ren, Hongjun
Dong, Zhi-Bing
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (06)
[2] Transition-Metal-Free C-H Hydroxylation of Carbonyl Compounds
Chaudhari, Moreshwar B.
Sutar, Yogesh
Malpathak, Shreyas
Hazra, Anirban
Gnanaprakasam, Boopathy
ORGANIC LETTERS, 2017, 19 (13) : 3628 - 3631
[3] Transition-Metal-Free Regioselective C-H Arylation of Heteroarenes
Choudhary, Shubhanjali
Yadav, Tanisha
Jaleel, Jarsha
Sharma, Pragati
Jaryal, Ritika
Bose, Shubahnakar
Kumar, Rakesh
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024,
[4] Transition-Metal-Free C-H Silylation: An Emerging Strategy
Tyagi, Arpana
Yadav, Naveen
Khan, Jabir
Singh, Sanjay
Kumar Hazra, Chinmoy
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (02) : 334 - 354
[5] Transition-Metal-Free Oxidative Aliphatic C-H Azidation
Zhang, Xiaofei
Yang, Haodong
Tang, Pingping
ORGANIC LETTERS, 2015, 17 (23) : 5828 - 5831
[6] Transition-Metal-Free Radical C-H Methylation of Quinoxalinones with TBHP
Rong, Xiaona
Jin, Liujun
Gu, Yugui
Liang, Guang
Xia, Qinqin
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (02) : 185 - 188
[7] Accessing Heterobiaryls through Transition-Metal-Free C-H Functionalization
Banik, Ananya
Paira, Rupankar
Shaw, Bikash Kumar
Vijaykumar, Gonela
Mandal, Swadhin K.
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (06): : 3236 - 3244
[8] Organocatalytic Enantioselective Regiodivergent C-H Bond Functionalization of 1-Naphthols with 1-Azadienes
Zhang, Chen
Cheng, Yuyu
Li, Fushuai
Luan, Yepeng
Li, Pengfei
Li, Wenjun
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (06) : 1286 - 1291
[9] Transition-Metal-Free Superbase-Promoted Stereoselective α-Vinylation of Ketones with Arylacetylenes: A General Strategy for Synthesis of β,γ-Unsaturated Ketones
Trofimov, Boris A.
Schmidt, Elena Yu.
Zorina, Nadezhda V.
Ivanova, Elena V.
Ushakov, Igor' A.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (16): : 6880 - 6886
[10] Transition-Metal-Free Addition of Acetylenes to Ketimines: the First Base-Catalyzed Ethynylation of the C=N Bond
Bidusenko, Ivan A.
Schmidt, Elena Yu
Ushakov, Igor A.
Trofimov, Boris A.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (35) : 4845 - 4849

← 1 2 3 4 5 →