A Highly Active Phosphine–Borane Organocatalyst for the Reduction of CO2 to Methanol Using Hydroboranes
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·TH...
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| Published in | Journal of the American Chemical Society Vol. 135; no. 25; pp. 9326 - 9329 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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26.06.2013
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| Abstract | 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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| AbstractList | 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 center dot SMe2 and BH3 center dot 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. 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. 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. 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. |
| Author | Légaré, Marc-André Maron, Laurent Fontaine, Frédéric-Georges Courtemanche, Marc-André |
| AuthorAffiliation | Université Laval Université de Toulouse |
| AuthorAffiliation_xml | – name: Université de Toulouse – name: Université Laval |
| Author_xml | – sequence: 1 givenname: Marc-André surname: Courtemanche fullname: Courtemanche, Marc-André organization: Université Laval – sequence: 2 givenname: Marc-André surname: Légaré fullname: Légaré, Marc-André organization: Université Laval – sequence: 3 givenname: Laurent surname: Maron fullname: Maron, Laurent email: frederic.fontaine@chm.ulaval.ca organization: Université de Toulouse – sequence: 4 givenname: Frédéric-Georges surname: Fontaine fullname: Fontaine, Frédéric-Georges email: frederic.fontaine@chm.ulaval.ca organization: Université Laval |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23750670$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1002/chem.201203226 10.1002/asia.200800388 10.1002/anie.201206165 10.1021/ja208969d 10.1002/anie.201006901 10.1039/c2cc30399j 10.1021/ja048911m 10.1002/anie.201107958 10.1021/cr068357u 10.1021/ja0647250 10.1021/ja305318c 10.1039/c1cc14641f 10.1039/c3cc41838c 10.1021/ja105320c 10.1021/om1008428 10.1039/b700658f 10.1021/jo801260f 10.1039/c3sc50145k 10.1002/anie.201107352 10.1021/ja0637494 10.1021/ja208760j 10.1002/anie.201202320 10.1002/anie.200901636 10.1002/anie.201000431 10.1002/anie.201000520 10.1039/c2cc35257e 10.1002/ejic.200800784 10.1021/ja2035514 10.1038/NCHEM.1089 10.1039/C0CS00129E 10.1002/anie.201201282 10.1002/anie.200905466 10.1021/ja9104792 10.1021/ja103982t 10.1002/anie.200806058 |
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| Keywords | HOMOGENEOUS HYDROGENATION CONVERSION HYDROSILYLATION FRUSTRATED LEWIS PAIRS CATALYST CARBON-DIOXIDE FIXATION |
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| Snippet | 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... 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... |
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| SubjectTerms | Boranes - chemistry Carbon Dioxide - chemistry Catalysis Chemistry Chemistry, Multidisciplinary Methanol - chemical synthesis Methanol - chemistry Molecular Structure Oxidation-Reduction Phosphines - chemistry Physical Sciences Science & Technology |
| Title | A Highly Active Phosphine–Borane Organocatalyst for the Reduction of CO2 to Methanol Using Hydroboranes |
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