One-Pot Three-Component Highly Selective Synthesis of Homoallylboronates by Using Metal-Free Catalysis

被引：40

作者：

Ibrahem, Ismail ^{[1
]}

Breistein, Palle ^{[1
]}

Cordova, Armando ^{[1
,2
,3
]}

机构：

[1] Mid Sweden Univ, Dept Nat Sci Engn & Math, SE-85170 Sundsvall, Sweden

[2] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

[3] Stockholm Univ, Berzelii Ctr EXSELENT, S-10691 Stockholm, Sweden

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 17期

关键词：

aldehydes; boron; conjugate addition; multicomponent reactions; organocatalysis; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; BORON CONJUGATE ADDITIONS; ASYMMETRIC BETA-BORATION; ENANTIOSELECTIVE HYDROBORATION; AMINO ALCOHOLS; BOND FORMATION; ESTERS; TERTIARY; DIBORON; SUBSTITUTION;

D O I：

10.1002/chem.201103572

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Metal-free selectivity: The first metal-free one-pot three-component highly chemo- and regioselective catalytic synthesis of homoallylboranes using simple N-heterocyclic carbenes (NHC) and amines is presented. The catalytic reaction between B 2(pin) 2, α,β-unsaturated aldehydes and 2-(triphenylphosphoranylidene)acetate esters proceeds through a catalytic metal-free β-boration/Wittig cascade sequence (see scheme). © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：5175 / 5179

页数：5

共 50 条

[1] One-pot three-component catalytic asymmetric synthesis of homoallylboronates
Ibrahem, Ismail
Afewerki, Samson
Breistein, Palle
Cordova, Armando
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[2] One-Pot Three-Component Catalytic Enantioselective Synthesis of Homoallylboronates
Ibrahem, Ismail
Breistein, Palle
Cordova, Armando
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) : 12036 - 12041
[3] A green and metal-free one-pot three-component synthesis of thiazolobenzimidazoles in sustainable deep eutectic solvent
Verma, Ankit
Sahay, Suhag S.
Nayak, Sushree S.
Bhagat, Shivani
Dani, Shilpa H.
Nayak, Bhojkumar
Pratap, Umesh R.
INORGANIC CHEMISTRY COMMUNICATIONS, 2024, 166
[4] One-pot, three-component, highly diastereoselective metal-free synthesis of 2,3,4,5-tetrasubstituted pyrrolidines
Crovetto, Luis
Rios, Ramon
SYNLETT, 2008, (12) : 1840 - 1844
[5] Metal-free greener method for the synthesis of densely functionalized pyrroles via a one-pot three-component reaction
Fatahpour, Maryam
Hazeri, Nourallah
Maghsoodlou, Malek Taher
Lashkari, Mojtaba
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (01) : 111 - 116
[6] Metal-free greener method for the synthesis of densely functionalized pyrroles via a one-pot three-component reaction
Maryam Fatahpour
Nourallah Hazeri
Malek Taher Maghsoodlou
Mojtaba Lashkari
Journal of the Iranian Chemical Society, 2019, 16 : 111 - 116
[7] Highly efficient metal-free one-pot synthesis of -aminophosphonates through reduction followed by Kabachnik-fields reaction using three-component system
Kolli, Murali Krishna
Elamathi, Palani
Chandrasekar, Govindasamy
Katta, Vishweshwar Rao
Raolji, Gajendrasinh Balvantsinh
SYNTHETIC COMMUNICATIONS, 2018, 48 (06) : 638 - 649
[8] Synthesis of highly functionalized thiophenes by three-component and one-pot reaction
Hassanabadi, Alireza
Hosseini-Tabatabaei, Mohammad R.
JOURNAL OF SULFUR CHEMISTRY, 2012, 33 (03) : 273 - 277
[9] Metal-Free One-Pot Synthesis of (Tetrahydro)Quinolines through Three-Component Assembly of Arenediazonium Salts, Nitriles, and Styrenes
Youn, So Won
Yoo, Huen Ji
Lee, Eun Mi
Lee, Seo Young
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (02) : 278 - 283
[10] Metal-Free One-Pot Synthesis of Benzofurans
Ghosh, Raju
Stridfeldt, Elin
Olofsson, Berit
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (29) : 8888 - 8892

← 1 2 3 4 5 →