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Literature DB >> 28739970

Design and reactions of a carbon Lewis base/boron Lewis acid frustrated Lewis pair.

Jennifer Möricke¹, Birgit Wibbeling¹, Constantin G Daniliuc¹, Gerald Kehr¹, Gerhard Erker².

Abstract

The conjugated dienamine 4 selectively adds Piers' borane [HB(C6F5)2] to give the enamine/borane system 5, which features a boratirane structure by internal enamine carbon Lewis base to boron Lewis acid interaction. Compound 5 behaves as a C/B frustrated Lewis pair and undergoes typical addition reactions to benzaldehyde, several nitriles and to sulfur dioxide.This article is part of the themed issue 'Frustrated Lewis pair chemistry'.

Entities: Chemical

Keywords: Lewis acid; Lewis base; borane; enamine; frustrated Lewis pair

Year: 2017 PMID： 28739970 PMCID： PMC5540844 DOI： 10.1098/rsta.2017.0015

Source DB: PubMed Journal: Philos Trans A Math Phys Eng Sci ISSN： 1364-503X Impact factor: 4.226

34 in total

1. Exploring the reactivity of carbon(0)/borane-based frustrated Lewis pairs.

Authors: Manuel Alcarazo; Catherine Gomez; Sigrid Holle; Richard Goddard
Journal: Angew Chem Int Ed Engl Date: 2010-08-02 Impact factor: 15.336

2. Nonmetal catalyzed hydrogenation of carbonyl compounds.

Authors: Daniel J Scott; Matthew J Fuchter; Andrew E Ashley
Journal: J Am Chem Soc Date: 2014-10-29 Impact factor: 15.419

3. Formylborane formation with frustrated Lewis pair templates.

Authors: Muhammad Sajid; Gerald Kehr; Constantin G Daniliuc; Gerhard Erker
Journal: Angew Chem Int Ed Engl Date: 2013-12-11 Impact factor: 15.336

4. Lewis acidity of organofluorophosphonium salts: hydrodefluorination by a saturated acceptor.

Authors: Christopher B Caputo; Lindsay J Hounjet; Roman Dobrovetsky; Douglas W Stephan
Journal: Science Date: 2013-09-20 Impact factor: 47.728

5. Dimeric aluminum-phosphorus compounds as masked frustrated Lewis pairs for small molecule activation.

Authors: Steffi Roters; Christian Appelt; Hauke Westenberg; Alexander Hepp; J Chris Slootweg; Koop Lammertsma; Werner Uhl
Journal: Dalton Trans Date: 2012-03-12 Impact factor: 4.390

6. Synthesis and reactivity of alkynyl-linked phosphonium borates.

Authors: Xiaoxi Zhao; Alan J Lough; Douglas W Stephan
Journal: Chemistry Date: 2011-05-05 Impact factor: 5.236

7. Nitrile insertion into a boryl-substituted five-membered zirconacycloallenoid: unexpected formation of a zwitterionic boratirane product.

Authors: Juri Ugolotti; Gerald Kehr; Roland Fröhlich; Stefan Grimme; Gerhard Erker
Journal: Chem Commun (Camb) Date: 2009-10-07 Impact factor: 6.222

Design and reactions of a carbon Lewis base/boron Lewis acid frustrated Lewis pair.

1. Exploring the reactivity of carbon(0)/borane-based frustrated Lewis pairs.

2. Nonmetal catalyzed hydrogenation of carbonyl compounds.

3. Formylborane formation with frustrated Lewis pair templates.

4. Lewis acidity of organofluorophosphonium salts: hydrodefluorination by a saturated acceptor.

5. Dimeric aluminum-phosphorus compounds as masked frustrated Lewis pairs for small molecule activation.

6. Synthesis and reactivity of alkynyl-linked phosphonium borates.

7. Nitrile insertion into a boryl-substituted five-membered zirconacycloallenoid: unexpected formation of a zwitterionic boratirane product.

8. Enamine/butadienylborane cycloaddition in the frustrated Lewis pair regime.

9. Rapid intramolecular heterolytic dihydrogen activation by a four-membered heterocyclic phosphane-borane adduct.

10. syn-1,2-carboboration of alkynes with borenium cations.

1. Frustrated Lewis pair chemistry.