Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

被引：28

作者：

Wang, Mei-Ling ^{[1
]}

Xu, Hui ^{[2
]}

Li, Han-Yuan ^{[2
]}

Ma, Biao ^{[2
]}

Wang, Zhen-Yu ^{[3
]}

Wang, Xing ^{[2
]}

Dai, Hui-Xiong ^{[2
,4
]}

机构：

[1] Univ Sci & Technol China, Nano Sci & Technol Inst, Suzhou 215123, Jiangsu, Peoples R China

[2] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, Shanghai 201203, Peoples R China

[3] Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Jiangsu, Peoples R China

[4] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 06期

基金：

中国国家自然科学基金;

关键词：

CATALYZED HECK; PALLADIUM; CHLORIDES; ARYLATION; CLEAVAGE;

D O I：

10.1021/acs.orglett.1c00296

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

引用

页码：2147 / 2152

页数：6

共 50 条

[21] Palladium-DABCO complex supported on γ-Fe2O3 magnetic nanoparticles: A new catalyst for C-C bond formation via Mizoroki-Heck cross-coupling reaction
Sobhani, Sara
Pakdin-Parizi, Zahra
APPLIED CATALYSIS A-GENERAL, 2014, 479 : 112 - 120
[22] Synthesis and Characterization of C,C-Type Palladacycles and Their Catalytic Application in Mizoroki-Heck Coupling Reaction
Lo, Chi Hou
Lee, Hon Man
ORGANOMETALLICS, 2018, 37 (07) : 1150 - 1159
[23] Ligand-Promoted C-3 Selective C-H Olefination of Pyridines with Pd Catalysts
Ye, Mengchun
Gao, Guo-Lin
Yu, Jin-Quan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (18) : 6964 - 6967
[24] Pd Nanoparticles Decorated on Jute Sticks: Dip-Catalyst of Suzuki-Miyaura and Mizoroki-Heck C-C Bond Formation Reactions in Water
Kalanthoden, Abdul Nasar
Shaikh, M. Nasiruzzaman
Aziz, Md Abdul
Rani, S. Kutti
CHEMISTRYSELECT, 2019, 4 (44): : 12832 - 12840
[25] Ultrasound promoted C-C bond formation: Heck reaction at ambient conditions in room temperature ionic liquids
Deshmukh, RR
Rajagopal, R
Srinivasan, KV
CHEMICAL COMMUNICATIONS, 2001, (17) : 1544 - 1545
[26] Palladium Nanoparticles Supported on Aminopropyl-Functionalized Clay as Efficient Catalysts for Phosphine-Free C-C Bond Formation via Mizoroki-Heck and Suzuki-Miyaura Reactions
Firouzabadi, Habib
Iranpoor, Nasser
Ghaderi, Arash
Ghavami, Maryam
Hoseini, S. Jafar
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2011, 84 (01) : 100 - 109
[27] A Study of the Step of Alkene Activation under Ligand-Free Conditions in the Mizoroki-Heck Reaction with Unreactive Aryl Chlorides
Kurokhtina, A. A.
Larina, E., V
Vidyaeva, E. V.
Lagoda, N. A.
Schmidt, A. F.
KINETICS AND CATALYSIS, 2021, 62 (02) : 307 - 314
[28] Stereospecific C-Glycosylation by Mizoroki-Heck Reaction: APowerful and Easy-to-Set-Up Synthetic Tool to Access - and -Aryl-C-Glycosides
Mabit, Thibaud
Siard, Aymeric
Legros, Frederic
Guillarme, Stephane
Martel, Arnaud
Lebreton, Jacques
Carreaux, Francois
Dujardin, Gilles
Collet, Sylvain
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (53) : 14069 - 14074
[29] Mizoroki-Heck reaction of 1,2-disubstituted aryl alkenes: Variables of synthesis, solvent and ligand modulation of reactivity
Bangar, Pronnoy G.
Jawalkar, Priyanka R.
Dumbre, Swapnil R.
Raut, Pallavi K.
Patil, Dharmaraj J.
Tv, Neethu
Sudhakaran, Shana
Iyer, Suresh
SYNTHETIC COMMUNICATIONS, 2020, 50 (24) : 3796 - 3803
[30] Total Synthesis of Syringin and Its Natural Analogues via C-C Bond Activation of Aryl Ketones
Wang, Zhen-Yu
Sun, Yi
Sun, Guo-Dong
Xu, Hui
Dai, Hui-Xiong
CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (24) : 3587 - 3592

← 1 2 3 4 5 →