Iridium-Catalyzed Regio- and Enantioselective Hydroarylation of Alkenyl Ethers by Olefin Isomerization

被引：102

作者：

Ebe, Yusuke ^{[1
]}

Onoda, Mitsuki ^{[1
]}

Nishimura, Takahiro ^{[1
]}

Yorimitsu, Hideki ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 20期

关键词：

alkenes; allylic compounds; C-H activation; iridium; isomerization; C-H BOND; ASYMMETRIC INTERMOLECULAR HYDROARYLATION; BRANCHED-SELECTIVE HYDROARYLATION; ORTHO-ALKYLATION; CHAIN-WALKING; VINYL ETHERS; AROMATIC KETIMINES; HECK ARYLATIONS; ACTIVATION; HYDROHETEROARYLATION;

D O I：

10.1002/anie.201702286

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Iridium-catalyzed hydroarylation of alkenyl ethers, such as allylic and homoallylic ethers, by C-H bond activation gave high yields of the corresponding addition products, where the aryl groups were selectively installed at the alpha-carbon atom to the alkoxy group. The reaction involves an isomerization of the alkenyl ethers into the corresponding 1-alkenyl ethers, which then undergo the regio-and enantioselective hydroarylation.

引用

页码：5607 / 5611

页数：5

共 81 条

[11] Iridium(I)-catalyzed asymmetric intermolecular hydroarylation of norbornene with benzamide [J].

Aufdenblatten, R ;

Diezi, S ;

Togni, A .

MONATSHEFTE FUR CHEMIE, 2000, 131 (12) :1345-1350

[12] 4',6-DICHLOROFLAVAN (BW683C), A NEW ANTI-RHINOVIRUS COMPOUND [J].

BAUER, DJ ;

SELWAY, JWT ;

BATCHELOR, JF ;

TISDALE, M ;

CALDWELL, IC ;

YOUNG, DAB .

NATURE, 1981, 292 (5821) :369-370

[13] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].

Colby, Denise A. ;

Tsai, Andy S. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825

[14] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[15] Branch-Selective Alkene Hydroarylation by Cooperative Destabilization: Iridium-Catalyzed ortho-Alkylation of Acetanilides [J].

Crisenza, Giacomo E. M. ;

Sokolova, Olga O. ;

Bower, John F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (49) :14866-14870

[16] Branch Selective Mural-type Alkene Hydroarylation Reactions [J].

Crisenza, Giacomo E. M. ;

Bower, John F. .

CHEMISTRY LETTERS, 2016, 45 (01) :2-9

[17] Branch-Selective, Iridium-Catalyzed Hydroarylation of Monosubstituted Alkenes via a Cooperative Destabilization Strategy [J].

Crisenza, Giacomo E. M. ;

McCreanor, Niall G. ;

Bower, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (29) :10258-10261

[18] Cobalt-catalyzed Branched-selective Addition of Aromatic Ketimines to Styrenes under Room-temperature Conditions [J].

Dong, Jinghua ;

Lee, Pin-Sheng ;

Yoshikai, Naohiko .

CHEMISTRY LETTERS, 2013, 42 (10) :1140-1142

[19] Addition of the ortho-C-H bonds of phenol across an olefin catalysed by a chiral iridium(I) diphosphine complex [J].

Dorta, R ;

Togni, A .

CHEMICAL COMMUNICATIONS, 2003, (06) :760-761

[20] Iridium-Catalyzed Branch-Selective Hydroarylation of Vinyl Ethers via C-H Bond Activation [J].

Ebe, Yusuke ;

Nishimura, Takahiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (18) :5899-5902

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