Intertwining Olefin Thianthrenation with Kornblum/Ganem Oxidations: Ene-type Oxidation to Furnish α,β-Unsaturated Carbonyls

被引：21

作者：

Angyal, Peter ^{[1
,2
]}

Kotschy, Andras M. ^{[1
,2
]}

Dudas, Adam ^{[1
,2
]}

Varga, Szilard ^{[1
]}

Soos, Tibor ^{[1
]}

机构：

[1] Res Ctr Nat Sci, Inst Organ Chem, Magyar Tudosok Korutja 2, H-1117 Budapest, Hungary

[2] Eotvos Lorand Univ, Hevesy Gyorgy PhD Sch Chem, Pazmany Peter Setany 1-A, H-1117 Budapest, Hungary

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 02期

关键词：

Alkenes; Alkenyl Electrophiles; C-H Functionalization; Oxidation; Thianthrenation; ALLYLIC OXIDATION; CONVENIENT METHOD; SEX-PHEROMONE; SELECTIVE METHOD; ALDEHYDES; ALKENES; AMINES; IDENTIFICATION; ALCOHOLS; ACETATES;

D O I：

10.1002/anie.202214096

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A widely applicable, practical, and scalable synthetic method for efficient ene-type double oxidation of alkenes is reported via a two-step alkenyl thianthrenium umpolung/Kornblum-Ganem oxidation strategy. This chemo- and stereoselective procedure allows easy access to various alpha,beta-unsaturated carbonyls that may be otherwise difficult or cumbersome to synthesize by conventional methods. For alpha-olefins, this metal-free transformation can be tuned according to synthetic needs to produce either the elusive (Z)-unsaturated aldehydes or their (E) counterparts. Moreover, this strategy has enabled streamlined synthesis of distinct butadienyl pheromones and kairomones.

引用

页数：5

共 70 条

[31]

Kurti L., 2005, STRATEGIC APPL NAMED, P250

[32] PREPARATION AND CHEMISTRY OF VINYL SULFONIUM YLIDES - NEW SYNTHETIC INTERMEDIATES [J].

LAROCHELLE, RW ;

TROST, BM ;

KREPSKI, L .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (08) :1126-+

[33] REACTIONS OF ORGANOLITHIUMS WITH ARYLSULFONIUM SALTS [J].

LAROCHELLE, RW ;

TROST, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (23) :6077-+

[34] Advances in asymmetric epoxidation of α,β-unsaturated carbonyl compounds:: The organocatalytic approach [J].

Lattanzi, Alessandra .

CURRENT ORGANIC SYNTHESIS, 2008, 5 (02) :117-133

[35] Palladium-Catalyzed Regioselective Aerobic Allylic C-H Oxygenation: Direct Synthesis of α,β-Unsaturated Aldehydes and Allylic Alcohols [J].

Li, Chunsheng ;

Chen, Huoji ;

Li, Jianxiao ;

Li, Meng ;

Liao, Jianhua ;

Wu, Wanqing ;

Jiang, Huanfeng .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (08) :1600-1604

[36]

Liu, 2022, ANGEW CHE, V134

[37] Visible-Light-Enabled Allylic C-H Oxidation: Metal-free Photocatalytic Generation of Enones [J].

Liu, Chao ;

Liu, Hui ;

Zheng, Xuan ;

Chen, Shanyi ;

Lai, Qihong ;

Zheng, Changlong ;

Huang, Mingqiang ;

Cai, Kaicong ;

Cai, Zhixiong ;

Cai, Shunyou .

ACS CATALYSIS, 2022, 12 (02) :1375-1381

[38] Intermolecular Metal-Free Cyclopropanation and Aziridination of Alkenes with XH2 (X=N, C) by Thianthrenation [J].

Liu, Ming-Shang ;

Du, Hai-Wu ;

Cui, Jian-Fang ;

Shu, Wei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (41)

[39] Metal-free allylic C-H nitrogenation, oxygenation, and carbonation of alkenes by thianthrenation [J].

Liu, Ming-Shang ;

Du, Hai-Wu ;

Shu, Wei .

CHEMICAL SCIENCE, 2022, 13 (04) :1003-1008

[40] Old tricks, new dogs: organocatalytic dienamine activation of α,β-unsaturated aldehydes [J].

Marcos, Vanesa ;

Aleman, Jose .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (24) :6812-6832

← 1 2 3 4 5 6 7 →