Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

被引：8

作者：

Gong, Pei-Xue ^{[1
]}

Xu, Fangning ^{[1
]}

Cheng, Lu ^{[1
]}

Gong, Xu ^{[1
]}

Zhang, Jie ^{[1
]}

Gu, Wei-Jin ^{[1
]}

Han, Wei ^{[1
,2
]}

机构：

[1] Nanjing Normal Univ, Sch Chem & Mat Sci, Nanjing 210023, Peoples R China

[2] Jiangsu Collaborat Innovat Ctr Biomed Funct Mat, Jiangsu Key Lab Biofunct Mat, Key Lab Appl Photochem, Nanjing 210023, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 48期

关键词：

LITHOCHOLIC ACID; TRIFLUOROMETHYLATION; CONVERSION; EFFICIENT; STRATEGY; ALKENES; KETONES; NICKEL;

D O I：

10.1039/d1cc01536b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A practical and general iron-catalyzed domino decarboxylation-oxidation of alpha,beta-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.

引用

页码：5905 / 5908

页数：4

共 64 条

[1] Installing the "magic methyl" - C-H methylation in synthesis [J].

Aynetdinova, Daniya ;

Callens, Mia C. ;

Hicks, Harry B. ;

Poh, Charmaine Y. X. ;

Shennan, Benjamin D. A. ;

Boyd, Alistair M. ;

Lim, Zhong Hui ;

Leitch, Jamie A. ;

Dixon, Darren J. .

CHEMICAL SOCIETY REVIEWS, 2021, 50 (09) :5517-5563

[2] The Methylation Effect in Medicinal Chemistry [J].

Barreiro, Eliezer J. ;

Kuemmerle, Arthur E. ;

Fraga, Carlos A. M. .

CHEMICAL REVIEWS, 2011, 111 (09) :5215-5246

[3] Decarboxylative functionalization of cinnamic acids [J].

Borah, Arun Jyoti ;

Yan, Guobing .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (30) :8094-8115

[4] SYNTHESIS OF DIARYLKETONES THROUGH CARBONYLATIVE COUPLING [J].

BRUNET, JJ ;

CHAUVIN, R .

CHEMICAL SOCIETY REVIEWS, 1995, 24 (02) :89-95

[5] Preparation of functional styrenes from biosourced carboxylic acids by copper catalyzed decarboxylation in PEG [J].

Cadot, Stephane ;

Rameau, Nelly ;

Mangematin, Stephane ;

Pinel, Catherine ;

Djakovitch, Laurent .

GREEN CHEMISTRY, 2014, 16 (06) :3089-3097

[6] The Friedel-Crafts syntheses [J].

Calloway, NO .

CHEMICAL REVIEWS, 1935, 17 (03) :327-392

[7] Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes [J].

Cao, Hui ;

Kuang, Yulong ;

Shi, Xiangcheng ;

Wong, Koi Lin ;

Tan, Boon Beng ;

Kwan, Jeric Mun Chung ;

Liu, Xiaogang ;

Wu, Jie .

NATURE COMMUNICATIONS, 2020, 11 (01)

[8] Lithocholic acid analogues, new and potent α-2,3-sialyltransferase inhibitors [J].

Chang, KH ;

Lee, L ;

Chen, J ;

Li, WS .

CHEMICAL COMMUNICATIONS, 2006, (06) :629-631

[9] New Acetophenone Derivatives from Acronychia oligophlebia and Their Anti-inflammatory and Antioxidant Activities [J].

Chen, Neng-Hua ;

Li, Wen ;

Zhong, Yuan-Lin ;

Niu, Qian-Wen ;

Li, Ying-Ying ;

Zhang, Yu-Bo ;

Li, Man-Mei ;

Li, Yao-Lan ;

Wang, Guo-Cai .

CHEMISTRY & BIODIVERSITY, 2018, 15 (05)

[10] Advances in the Synthesis of Methylated Products through Indirect Approaches [J].

Chen, Yantao .

ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (05) :998-1014

← 1 2 3 4 5 6 7 →