Ir(III)-Catalyzed Direct C-H Functionalization of Arylphosphine Oxides: A Strategy for MOP-Type Ligands Synthesis

被引：63

作者：

Liu, Zhong ^{[1
]}

Wu, Ji-Qiang ^{[1
]}

Yang, Shang-Dong ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 19期

关键词：

N-SULFONATED IMINES; DIAZO-COMPOUNDS; BOND FUNCTIONALIZATION; CARBENOID FUNCTIONALIZATION; RH(III)-CATALYZED SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; BAYLIS-HILLMAN; BENZOIC-ACIDS; MILD;

D O I：

10.1021/acs.orglett.7b02710

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diazo compounds as coupling partners are efficiently applied to Ir(III)-catalyzed direct C-H functionalization of arylphosphine oxides. Involving C-H activation, carbene insertion, and tautomerism, this reaction proceeds under mild conditions, thus proving an approach to the synthesis of MOP-type ligand precursor in a single step. The utility of this transformation has been further demonstrated in ligand synthesis as well as in the construction of phosphole framework.

引用

页码：5434 / 5437

页数：4

共 81 条

[1]

[Anonymous], 2015, ANGEW CHE

[2] Palladium-Catalyzed Synthesis of Six-Membered Benzofuzed Phosphacycles via Carbon Phosphorus Bond Cleavage [J].

Baba, Katsuaki ;

Tobisu, Mamoru ;

Chatani, Naoto .

ORGANIC LETTERS, 2015, 17 (01) :70-73

[3] Palladium-Catalyzed Direct Synthesis of Phosphole Derivatives from Triarylphosphines through Cleavage of Carbon-Hydrogen and Carbon-Phosphorus Bonds [J].

Baba, Katsuaki ;

Tobisu, Mamoru ;

Chatani, Naoto .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (45) :11892-11895

[4] Cascade C-H Functionalization/Amidation Reaction for Synthesis of Azepinone Derivatives [J].

Bai, Peng ;

Huang, Xing-Fen ;

Xu, Guo-Dong ;

Huang, Zhi-Zhen .

ORGANIC LETTERS, 2016, 18 (13) :3058-3061

[5] P, N ligands in asymmetric catalysis [J].

Carroll, Michael P. ;

Guiry, Patrick J. .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) :819-833

[6] Palladium-catalyzed ortho-alkenylation of aryl hydrogen phosphates using a new mono-phosphoric acid directing group [J].

Chan, Li Yan ;

Kim, Sunggak ;

Ryu, Taekyu ;

Lee, Phil Ho .

CHEMICAL COMMUNICATIONS, 2013, 49 (41) :4682-4684

[7] Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates [J].

Chan, Wai-Wing ;

Lo, Siu-Fung ;

Zhou, Zhongyuan ;

Yu, Wing-Yiu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13565-13568

[8] Enantioselective C-H Annulation of Indoles with Diazo Compounds through a Chiral Rh(III) Catalyst [J].

Chen, Xiaohong ;

Yang, Shujing ;

Li, Helong ;

Wang, Bo ;

Song, Guoyong .

ACS CATALYSIS, 2017, 7 (04) :2392-2396

[9] Silver-Mediated Oxidative C-H/P-H Functionalization: An Efficient Route for the Synthesis of Benzo[b]phosphole Oxides [J].

Chen, Yun-Rong ;

Duan, Wei-Liang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (45) :16754-16757

[10] Rh(III)-catalyzed C-H activation/[4+3] cycloaddition of benzamides and vinylcarbenoids: facile synthesis of azepinones [J].

Cui, Sunliang ;

Zhang, Yan ;

Wang, Dahai ;

Wu, Qifan .

CHEMICAL SCIENCE, 2013, 4 (10) :3912-3916

← 1 2 3 4 5 6 7 8 9 →