New Bisoxazoline Ligands Enable Enantioselective Electrocatalytic Cyanofunctionalization of Vinylarenes

被引：194

作者：

Fu, Niankai ^{[1
]}

Song, Lu ^{[1
]}

Liu, Jinjian ^{[1
]}

Shen, Yifan ^{[1
]}

Siu, Juno C. ^{[1
]}

Lin, Song ^{[1
]}

机构：

[1] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 37期

关键词：

REDUCTIVE ELIMINATION; CYCLIZATION REACTIONS; ALKENES; AMINO; BONDS; DIFUNCTIONALIZATION; DIETHYLZINC; PHOSPHINES; PHOTOREDOX; COMPLEXES;

D O I：

10.1021/jacs.9b03296

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In contrast to the rapid growth of synthetic electrochemistry in recent years, enantioselective catalytic methods powered by electricity remain rare. In this work, we report the development of a highly enantioselective method for the electrochemical cyanophosphinoylation of vinylarenes. A new family of serine-derived chiral bisoxazolines with ancillary coordination sites were identified as optimal ligands.

引用

页码：14480 / 14485

页数：6

共 77 条

[1] PENTACOORDINATE COPPER-COMPLEXES OF NITROGEN-SULFUR DONORS - STRUCTURAL CHEMISTRY OF 2 COMPLEXES OF BIS(2-(2-BENZIMIDAZOLYL)ETHYL) SULFIDE WITH THE SULFUR ALTERNATIVELY IN EQUATORIAL AND AXIAL COORDINATION MODES [J].

ADDISON, AW ;

BURKE, PJ ;

HENRICK, K ;

RAO, TN ;

SINN, E .

INORGANIC CHEMISTRY, 1983, 22 (24) :3645-3653

[2] Coordination diversity of copper(II) phosphoryl-functionalized salicylaldiminates: Effect of the length of the pendant phosphoryl arm [J].

Aleksanyan, Diana V. ;

Nelyubina, Yulia V. ;

Dmitrienko, Artem O. ;

Bushmarinov, Ivan S. ;

Klemenkova, Zinaida S. ;

Kozlov, Vladimir A. .

POLYHEDRON, 2015, 85 :295-301

[3] Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes [J].

Anthony, David ;

Lin, Qiao ;

Baudet, Judith ;

Diao, Tianning .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (10) :3198-3202

[4] Halogen and Chalcogen Cation Pools Stabilized by DMSO. Versatile Reagents for Alkene Difunctionalization [J].

Ashikari, Yosuke ;

Shimizu, Akihiro ;

Nokami, Toshiki ;

Yoshida, Jun-ichi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16070-16073

[5] Catalytic Enantioselective Alkene Aminohalogenation/Cyclization Involving Atom Transfer [J].

Bovino, Michael T. ;

Chemler, Sherry R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (16) :3923-3927

[6] Direct observation of CuI/CuIII redox steps relevant to Ullmann-type coupling reactions [J].

Casitas, Alicia ;

King, Amanda E. ;

Parella, Teodor ;

Costas, Miquel ;

Stahl, Shannon S. ;

Ribas, Xavi .

CHEMICAL SCIENCE, 2010, 1 (03) :326-330

[7] Heterocycle synthesis by copper facilitated addition of heteroatoms to alkenes, alkynes and arenes [J].

Chemler, Sherry R. ;

Fuller, Peter H. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1153-1160

[8] Rhodium-Catalyzed Enantioselective Radical Addition of CX4 Reagents to Olefins [J].

Chen, Bo ;

Fang, Cheng ;

Liu, Peng ;

Ready, Joseph M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (30) :8780-8784

[9] Electrocatalytic Aziridination of Alkenes Mediated by n-Bu4NI: A Radical Pathway [J].

Chen, Jie ;

Yan, Wei-Qing ;

Lam, Chiu Marco ;

Zeng, Cheng-Chu ;

Hu, Li-Ming ;

Little, R. Daniel .

ORGANIC LETTERS, 2015, 17 (04) :986-989

[10] Recent Progress in Visible-Light Photoredox-Catalyzed Intermolecular 1,2-Difunctionalization of Double Bonds via an ATRA-Type Mechanism [J].

Courant, Thibaut ;

Masson, Geraldine .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :6945-6952

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