Direct Catalytic Anti-Markovnikov Hydroetherification of Alkenols

被引：309

作者：

Hamilton, David S. ^{[1
]}

Nicewicz, David A. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 45期

关键词：

NUCLEOPHILE-OLEFIN COMBINATION; PHOTO-NOCAS REACTION; ELECTRON-TRANSFER; RADICAL CATIONS; 9-MESITYL-10-METHYLACRIDINIUM ION; PHOTOCATALYTIC OXYGENATION; HYDROAMINATION; ALKYNES; PHOTOADDITION; VINYLARENES;

D O I：

10.1021/ja309635w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct intramolecular anti-Markovnikov hydroetherification reaction of alkenols is described. By employing Catalytic quantities of commercially available 9-mesityl-10-methylacridinium perchlorate and 2-phenyl-malononitrile as a redox-cycling source of a H-atom, we report the anti-Markovnikov hydroetherification of alkenes with complete regioselectivity, In addition, we present results demonstrating that this novel catalytic system can be applied to the anti-Markovnikov hydrolactonization of alkenoic acids.

引用

页码：18577 / 18580

页数：4

共 33 条

[1] Photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction .12. Factors controlling the regiochemistry of the reaction with alcohol as the nucleophile
Arnold, DR
Chan, MSW
McManus, KA
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (11): : 2143 - 2166
[2] Enantiodifferentiating anti-Markovnikov photoaddition of alcohols to 1,1-diphenylalkenes sensitized by chiral naphthalenecarboxylates
Asaoka, S
Kitazawa, T
Wada, T
Inoue, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (37) : 8486 - 8498
[3] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends
Beller, M
Seayad, J
Tillack, A
Jiao, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) : 3368 - 3398
[4] Stereochemical memory effects in alkene radical cation/anion contact ion pairs: Effect of substituents, and models for diastereoselectivity
Crich, D
Ranganathan, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (27) : 9924 - 9929
[5] Tandem polar/radical crossover sequences for the formation of fused and bridged bicyclic nitrogen heterocycles involving radical ionic chain reactions, and alkene radical cation intermediates, performed under reducing conditions: Scope and limitations
Crich, D
Ranganathan, K
Neelamkavil, S
Huang, XH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) : 7942 - 7947
[6] Enantioselective alkene radical cations reactions
Crich, David
Shirai, Michio
Brebion, Franck
Rumthao, Sochanchingwung
[J]. TETRAHEDRON, 2006, 62 (27) : 6501 - 6518
[7] Generation of alkene radical cations by heterolysis of β-substituted radicals:: Mechanism, stereochemistry, and applications in synthesis
Crich, David
Brebion, Franck
Suk, Dae-Hwan
[J]. RADICALS IN SYNTHESIS I: METHODS AND MECHANISMS, 2006, 263 : 1 - 38
[8] Primary Alcohols from Terminal Olefins: Formal Anti-Markovnikov Hydration via Triple Relay Catalysis
Dong, Guangbin
Teo, Peili
Wickens, Zachary K.
Grubbs, Robert H.
[J]. SCIENCE, 2011, 333 (6049) : 1609 - 1612
[9] Electron-transfer state of 9-mesityl-10-methylacridinium ion with a much longer lifetime and higher energy than that of the natural photosynthetic reaction center
Fukuzumi, S
Kotani, H
Ohkubo, K
Ogo, S
Tkachenko, NV
Lemmetyinen, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) : 1600 - 1601
[10] ANTI-MARKOVNIKOV ADDITION OF NUCLEOPHILES TO A NONCONJUGATED OLEFIN VIA SINGLE ELECTRON-TRANSFER PHOTOCHEMISTRY
GASSMAN, PG
BOTTORFF, KJ
[J]. TETRAHEDRON LETTERS, 1987, 28 (45) : 5449 - 5452

← 1 2 3 4 →