New Tetraphosphorus Ligands for Highly Linear Selective Hydroformylation of Allyl and Vinyl Derivatives

被引:31
作者
Cai, Chaoxian [1 ,2 ]
Yu, Shichao [1 ,2 ]
Cao, Bonan [1 ,2 ]
Zhang, Xumu [1 ,2 ]
机构
[1] Rutgers State Univ, Dept Med Chem, Piscataway, NJ 08854 USA
[2] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
基金
美国国家科学基金会;
关键词
hydroformylation; ligand; olefin; regioselectivity; rhodium; RHODIUM-CATALYZED HYDROFORMYLATION; REGIOSELECTIVE ISOMERIZATION-HYDROFORMYLATION; ASYMMETRIC HYDROFORMYLATION; RAPID HYDROFORMYLATION; METAL COORDINATION; INTERNAL OLEFINS; COMPLEXES; ALKENES;
D O I
10.1002/chem.201201396
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New tetraphosphorus ligands have been developed and applied in the rhodium-catalyzed regioselective hydroformylation of a variety of functionalized allyl and vinyl derivatives. Remarkably high linear selectivity was obtained by these tetraphosphorus ligands. The ligand that bears strong electron-withdrawing 2,4-difluorophenyl groups is the most effective one in affording linear aldehydes. The Rh/tetraphosphorus ligand catalyst is highly effective to produce linear aldehydes from functionalized allyl derivatives with heteroatoms or aromatic groups directly adjacent to the allyl group. For vinyl derivatives, the ligand is highly linear selective for acrylic derivatives, styrene, vinyl pyridine, and vinyl phthalimide. Linear to branch ratios of 26:1 and 10:1 were obtained for the hydroformylation of styrene and allyl cyanide, respectively.
引用
收藏
页码:9992 / 9998
页数:7
相关论文
共 52 条
[1]  
Axtell A.T., 2005, Angew. Chem, V117, P5984, DOI DOI 10.1016/J.ATHORACSUR.2019.12.077
[2]   Highly regio- and enantioselective asymmetric hydroformylation of olefins mediated by 2,5-disubstituted phospholane ligands [J].
Axtell, AT ;
Cobley, CJ ;
Klosin, J ;
Whiteker, GT ;
Zanotti-Gerosa, A ;
Abboud, KA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (36) :5834-5838
[3]  
Billig E., 1988, US Patent, Patent No. [4,769,498, 4769498]
[4]   HYDROFORMYLATION OF OLEFINS CATALYZED BY ALKENE COMPLEXES OF PLATINUM(0) [J].
BOTTEGHI, C ;
PAGANELLI, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 417 (1-2) :C41-C45
[5]  
Breit B, 2001, SYNTHESIS-STUTTGART, P1
[6]   HOMOGENEOUS HYDROFORMYLATION OF ALKENES WITH HYDRIDOCARBONYLTRIS-(TRIPHENYLPHOSPHINE)RHODIUM(I) AS CATALYST [J].
BROWN, CK ;
WILKINSON, G .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1970, (17) :2753-+
[7]  
BURKE PM, 1997, Patent No. 9733854
[8]   Unraveling the origin of regioselectivity in rhodium diphosphine catalyzed hydroformylation.: A DFT QM/MM study [J].
Carbó, JJ ;
Maseras, F ;
Bo, C ;
van Leeuwen, PWNM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7630-7637
[9]   Electron withdrawing substituents on equatorial and apical phosphines have opposite effects on the regioselectivity of rhodium catalyzed hydroformylation [J].
Casey, CP ;
Paulsen, EL ;
Beuttenmueller, EW ;
Proft, BR ;
Petrovich, LM ;
Matter, BA ;
Powell, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) :11817-11825
[10]   DIPHOSPHINES WITH NATURAL BITE ANGLES NEAR 120-DEGREES INCREASE SELECTIVITY FOR NORMAL-ALDEHYDE FORMATION IN RHODIUM-CATALYZED HYDROFORMYLATION [J].
CASEY, CP ;
WHITEKER, GT ;
MELVILLE, MG ;
PETROVICH, LM ;
GAVNEY, JA ;
POWELL, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5535-5543