A Highly Active Phosphine–Borane Organocatalyst for the Reduction of CO2 to Methanol Using Hydroboranes | Zendy

MarcAndré Courtemanche | Zendy; MarcAndré Légaré | Zendy; Laurent Maron | Zendy; FrédéricGeorges Fontaine | Zendy

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A Highly Active Phosphine–Borane Organocatalyst for the Reduction of CO₂ to Methanol Using Hydroboranes

Author(s) -

MarcAndré Courtemanche,

MarcAndré Légaré,

Laurent Maron,

FrédéricGeorges Fontaine

Publication year - 2013

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja404585p

Subject(s) - chemistry , borane , phosphine , methanol , reagent , hydrolysis , turnover number , catalysis , organic chemistry , catechol , organocatalysis , nonane , medicinal chemistry , enantioselective synthesis

In this work, we report that organocatalyst 1-Bcat-2-PPh2-C6H4 ((1); cat = catechol) acts as an ambiphilic metal-free system for the reduction of carbon dioxide in presence of hydroboranes (HBR2 = HBcat (catecholborane), HBpin (pinacolborane), 9-BBN (9-borabicyclo[3.3.1]nonane), BH3·SMe2 and BH3·THF) to generate CH3OBR2 or (CH3OBO)3, products that can be readily hydrolyzed to methanol. The yields can be as high as 99% with exclusive formation of CH3OBR2 or (CH3OBO)3 with TON (turnover numbers) and TOF (turnover frequencies) reaching >2950 and 853 h(-1), respectively. Furthermore, the catalyst exhibits "living" behavior: once the first loading is consumed, it resumes its activity on adding another loading of reagents.

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