Large P-P Distance Diphosphines and Their Monophosphine Analogues as Ligands in the Palladium-Catalyzed Telomerization of 1,3-Butadiene and Methanol

被引:26
|
作者
Tschan, Mathieu J. -L. [1 ]
Lopez-Valbuena, Josep-Maria [1 ]
Freixa, Zoraida [1 ]
Launay, Helene [2 ]
Hagen, Henk [2 ]
Benet-Buchholz, Jordi [1 ]
van Leeuwen, Piet W. N. M. [1 ]
机构
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[2] Dow Benelux BV, NL-4530 AA Terneuzen, Netherlands
关键词
EFFICIENT CATALYST; FINE CHEMICALS; BUTADIENE; COMPLEXES; 1,3-DIENES; ALCOHOLS; DIMERIZATION; REGIOSELECTIVITY; OCTADIENYL; SPANPHOS;
D O I
10.1021/om100980m
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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-buty1-4-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.
引用
收藏
页码:792 / 799
页数:8
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