Intermolecular Hydroalkoxylation of Terminal Alkynes Catalyzed by a Dipyrrinato Rhodium(I) Complex with Unusual Selectivity

被引：19

作者：

Lam, Raphael H. ^{[1
,2
]}

Walker, D. Barney ^{[1
,2
]}

Tucker, Matthew H. ^{[1
]}

Gatus, Mark R. D. ^{[1
,2
]}

Bhadbhade, Mohan ^{[3
]}

Messerle, Barbara A. ^{[1
,2
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

[2] Macquarie Univ, Dept Chem & Biomol Sci, N Ryde, NSW 2109, Australia

[3] Univ New S Wales, Mark Wainwright Analyt Ctr, Sydney, NSW 2052, Australia

来源：

ORGANOMETALLICS | 2015年 / 34卷 / 17期

基金：

澳大利亚研究理事会;

关键词：

ENOL ETHERS; DIASTEREOSELECTIVE SYNTHESIS; STEREOCONTROLLED SYNTHESIS; ASYMMETRIC-SYNTHESIS; RH(I) COMPLEXES; BODIPY DYES; EFFICIENT; DERIVATIVES; CYCLIZATION; METATHESIS;

D O I：

10.1021/acs.organomet.5b00561

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An operationally simple and atom-economical method for the E-selective preparation of enol ethers is described. A novel dicarbonyl(S-phenyldipyrrinato)rhodium complex, 2, was prepared in four synthetic steps, characterized by X-ray crystallography and NMR spectroscopy, and then investigated as a catalyst for the intermolecular hydro-alkoxylation of terminal alkynes. Solvent and substrate studies were used to gain insight into the mechanism of the reaction. Cyclic voltammetry was also used to investigate the electronic properties of 2. The rhodium(I)-catalyzed intermolecular alkyne hydroalkoxylation reaction reported here mediates excellent substrate transformation with a high degree of E/Z selectivity which is opposite to that reported previously using alternative catalysts.

引用

页码：4312 / 4317

页数：6

共 46 条

[1] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[2]

[Anonymous], 2001, SADABS

[3]

[Anonymous], 2001, APEX2 SAINT

[4] Fluorescent indicators based on BODIPY [J].

Boens, Noel ;

Leen, Volker ;

Dehaen, Wim .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) :1130-1172

[5] Cooperative Friedel-Crafts catalysis in heterobimetallic regime:: Alkylation of aromatics by π-activated alcohols [J].

Choudhury, J ;

Podder, S ;

Roy, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6162-6163

[6] Cooperative Catalysis: Large Rate Enhancements with Bimetallic Rhodium Complexes [J].

Choy, Sandra W. S. ;

Page, Michael J. ;

Bhadbhade, Mohan ;

Messerle, Barbara A. .

ORGANOMETALLICS, 2013, 32 (17) :4726-4729

[7] Mechanism and Origins of Z Selectivity of the Catalytic Hydroalkoxylation of Alkynes via Rhodium Vinylidene Complexes To Produce Enol Ethers [J].

Dang, Yanfeng ;

Qu, Shuanglin ;

Wang, Zhi-Xiang ;

Wang, Xiaotai .

ORGANOMETALLICS, 2013, 32 (09) :2804-2813

[8] Hetero-Diels-Alder Reaction of Phosphorylated Nitroso Alkenes with Enol Ethers on Water: A Clean Approach Toward 1,2-Oxazine Derivatives [J].

de los Santos, Jesus M. ;

Ignacio, Roberto ;

Es Sbai, Zouhair ;

Aparicio, Domitila ;

Palacios, Francisco .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) :7607-7615

[9] A metathesis-based approach to the synthesis of furans [J].

Donohoe, Timothy J. ;

Fishlock, Lisa P. ;

Lacy, Adam R. ;

Procopiou, Panayiotis A. .

ORGANIC LETTERS, 2007, 9 (06) :953-956

[10] CHEMISTRY OF ENOL ETHERS [J].

EFFENBER.F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (05) :295-&

← 1 2 3 4 5 →