Large P−P Distance Diphosphines and Their Monophosphine Analogues as Ligands in the Palladium-Catalyzed Telomerization of 1,3-Butadiene and Methanol
The potential of diphosphines based on a dibenzodioxocin or benzofurobenzofuran backbone possessing large P−P distances was studied for the selective telomerization of 1,3-butadiene with methanol under commercially relevant process conditions to obtain 1-methoxyocta-2,7-diene (1-MOD). They were foun...
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Published in | Organometallics Vol. 30; no. 4; pp. 792 - 799 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
28.02.2011
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | The potential of diphosphines based on a dibenzodioxocin or benzofurobenzofuran backbone possessing large P−P distances was studied for the selective telomerization of 1,3-butadiene with methanol under commercially relevant process conditions to obtain 1-methoxyocta-2,7-diene (1-MOD). They were found to act as monophosphines. New bulky monophosphine analogues of the same backbone and ferrocene were also evaluated. Several ligands showed improved selectivity and yield compared to the benchmark ligand PPh3 and monoxantphos. Especially 1,6-bis(diphenylphosphino)-5a,10b-dihydro-5a,10b-dimethyl-3,8-dimethylbenzofuro[3,2-b]benzofuran (3) and, 2,10-di-tert-butyl-4-diphenylphosphino-6,12-methano-12H-dibenzo[2,1-d:1′,2′′-g][1,3]dioxocin (7), a diphosphine and a monophosphine, respectively, stand out as excellent ligands in terms of yield, selectivity, and stability. |
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ISSN: | 0276-7333 1520-6041 |
DOI: | 10.1021/om100980m |