Iron-Photocatalyzed Decarboxylative Alkylation of Carboxylic Acids with Morita-Baylis-Hillman Acetates

被引：0

作者：

Yin, Yanli ^{[1
,2
]}

Chen, Fang ^{[1
]}

Chen, Dong ^{[3
]}

Xie, Peizhong ^{[4
]}

Wang, Dongping ^{[1
]}

Loh, Teck-Peng ^{[1
]}

机构：

[1] Henan Univ Technol, Coll Adv Interdisciplinary Sci & Technol CAIST, Zhengzhou 450001, Henan, Peoples R China

[2] Henan Normal Univ, Sch Chem & Chem Engn, Pingyuan Lab, Xinxiang 453007, Henan, Peoples R China

[3] Henan Univ Engn, Coll Mat Engn, Henan Int Joint Lab Rare Earth Composite Mat, Zhengzhou 450001, Henan, Peoples R China

[4] Nanjing Tech Univ, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 27卷 / 01期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

PHOTOREDOX CATALYSIS; COUPLING REACTIONS; LIGHT; ALKENES; DERIVATIVES; ARYLATION; AMINES; LIGAND;

D O I：

10.1021/acs.orglett.4c04267

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present an iron-photocatalyzed decarboxylative alkylation strategy involving carboxylic acids and Morita-Baylis-Hillman (MBH) acetates to synthesize E-type tri- and tetrasubstituted alkenes with moderate to excellent stereoselectivity (E/Z ratio up to >19:1). This method is applicable to a broad range of structurally diverse primary, secondary, and tertiary alkyl carboxylic acids, as well as complex pharmaceutical and natural carboxylic acids, achieving efficient alkylation of various MBH acetates under mild conditions (>60 examples, with yields up to 96%). This approach offers a powerful strategy for streamlined alkylation.

引用

页码：269 / 274

页数：6

共 50 条

[21] Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates
Peng Jing
Cui HaiLei
Chen YingChun
SCIENCE CHINA-CHEMISTRY, 2011, 54 (01) : 81 - 86
[22] Mechanistic implications in the Morita-Baylis-Hillman alkylation: Isolation and characterization of an intermediate
Krafft, ME
Haxell, TFN
Seibert, KA
Abboud, KA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (13) : 4174 - 4175
[23] Organocatalytic asymmetric allylic alkylation of sulfonylimidates with Morita-Baylis-Hillman carbonates
PENG Jing
Department of Medicinal Chemistry
Science China(Chemistry), 2011, (01) : 81 - 86
[24] Organocatalyzed Decarboxylative Trichloromethylation of Morita-Baylis-Hillman Adducts in Batch and Continuous Flow
Enevoldsen, Martin V.
Overgaard, Jacob
Pedersen, Maja S.
Lindhardt, Anders T.
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (05) : 1204 - 1208
[25] Diels-Alder dimerization of Morita-Baylis-Hillman acetates catalyzed by organocatalysts
Deng, Hong-Ping
Wei, Yin
Shi, Min
RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (01) : 5 - 18
[26] Iridium-catalyzed Allylation of Morita-Baylis-Hillman Acetates with Indolinone Compounds
Chen, Xiangmeng
Zhang, Yaqi
Liang, Hao
Chen, Bin
Ouyang, Jiasheng
He, Xiaobo
Qian, Xu
Pu, Xiaoyun
Pan, Bendu
Qiu, Liqin
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2020, 41 (10): : 2216 - 2224
[27] Iron-photocatalyzed double decarboxylative coupling reactions of alkynoic acids and alkyl carboxylic acids: access to alkylated alkynes
Kang, Hyemin
An, Seunghwan
Lee, Sunwoo
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (20) : 5151 - 5157
[28] Enantioselective O-allylic alkylation of Morita-Baylis-Hillman carbonates with oxime
HU ZeKai
Science in China(Series B:Chemistry), 2009, (09) : 1309 - 1313
[29] Enantioselective O-allylic alkylation of Morita-Baylis-Hillman carbonates with oxime
ZeKai Hu
HaiLei Cui
Kun Jiang
YingChun Chen
Science in China Series B: Chemistry, 2009, 52 : 1309 - 1313
[30] Asymmetric N-Allylic Alkylation of Hydrazones with Morita-Baylis-Hillman Carbonates
Yao, Lu
Wang, Chun-Jiang
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (2-3) : 384 - 388

← 1 2 3 4 5 →