Photoinduced addition and addition-elimination reactions of perfluoroalkyl iodides to electron-deficient olefins

被引：38

作者：

Yajima, Tomoko ^{[1
]}

Jahan, Ishrat ^{[1
]}

Tonoi, Takayuki ^{[1
]}

Shinmen, Manami ^{[1
]}

Nishikawa, Aya ^{[1
]}

Yamaguchi, Kanako ^{[1
]}

Sekine, Izumi ^{[1
]}

Nagano, Hajime ^{[1
]}

机构：

[1] Ochanomizu Univ, Dept Chem, Bunkyo Ku, Otsuka, Tokyo 1128610, Japan

来源：

TETRAHEDRON | 2012年 / 68卷 / 34期

关键词：

Iodoperfluoroalkylation; Addition-elimination reaction; Electron-deficient olefin; Photoinduced radical reaction; SILYL ENOL ETHERS;

D O I：

10.1016/j.tet.2012.06.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photoinduced radical perfluoroalkylation of various simple electron-deficient olefins was achieved in the presence of an aqueous Na2S2O3 solution. The reactions proceeded smoothly to give addition or addition elimination products. The ability of the products to be used as radical precursors or Michael acceptors was also demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：6856 / 6861

页数：6

共 50 条

[21] Alkylation of Electron-Deficient Olefins through Conjugate Addition of Organozinc Reagents: An Update
Baruah, Biswajita
Deb, Mohit L.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (42) : 5756 - 5766
[22] Samarium triiodide-catalyzed conjugate addition of indoles with electron-deficient olefins
Zhan, ZP
Yang, RF
Lang, K
TETRAHEDRON LETTERS, 2005, 46 (22) : 3859 - 3862
[23] Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3
Alam, MM
Varala, R
Adapa, SR
TETRAHEDRON LETTERS, 2003, 44 (27) : 5115 - 5119
[24] An addition of benzylic sp3 C-H to electron-deficient olefins
Li, Hong-Ying
Xing, Li-Juan
Xu, Tong
Wang, Peng
Liu, Rui-Hua
Wang, Bin
TETRAHEDRON LETTERS, 2013, 54 (08) : 858 - 860
[25] Catalyst-Controlled, Enantioselective, and Diastereodivergent Conjugate Addition of Aldehydes to Electron-Deficient Olefins
Kan, S. B. Jennifer
Maruyama, Hiroki
Akakura, Matsujiro
Kano, Taichi
Maruoka, Keiji
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (32) : 9487 - 9491
[26] Microwave-Assisted Conjugate Addition of Pyrrole on Electron-Deficient Nitro-Olefins
Kusurkar, Radhika S.
Alkobati, Nabil A. H.
SYNTHETIC COMMUNICATIONS, 2010, 40 (03) : 320 - 327
[27] ADDITION-ELIMINATION REACTIONS BETWEEN PHENYLLITHIUM AND SOME PERFLUOROVINYLETHER COMPOUNDS
CHEN, LS
TAMBORSKI, C
JOURNAL OF FLUORINE CHEMISTRY, 1982, 20 (03) : 341 - 348
[28] CYCLO-ADDITION VS MICHAEL ADDITION IN THE METAL HALIDE AMINE-INDUCED REACTIONS OF ALPHA-(ALKYLIDENEAMINO) ESTERS WITH ELECTRON-DEFICIENT OLEFINS
KANEMASA, S
YOSHIOKA, M
TSUGE, O
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (03) : 869 - 874
[29] TRANSFORMATIONS IN SIDE-CHAIN OF EPIQUINIDINE IN ADDITION-ELIMINATION REACTIONS
SUSZKO, J
THIEL, J
ROCZNIKI CHEMII, 1975, 49 (01): : 47 - 54
[30] Photoinduced electron transfer from N-methylpyrrolidine to ketones and radical addition to an electron-deficient alkene
Hoffmann, N
Görner, H
CHEMICAL PHYSICS LETTERS, 2004, 383 (5-6) : 451 - 455

← 1 2 3 4 5 →