Metal-Free Chemoselective Oxidative Dehomologation or Direct Oxidation of Alcohols: Implication for Biomass Conversion

被引:34
作者
Kim, Sun Min [1 ]
Shin, Hun Yi [1 ]
Kim, Dong Wan [1 ]
Yang, Jung Woon [1 ]
机构
[1] Sungkyunkwan Univ, Dept Energy Sci, 2066 Seobu Ro, Suwon 440746, Gyeonggi Do, South Korea
关键词
biomass conversion; chemoselectivity; dehomologation; lignin; oxidation; C-C BOND; CARBON-CARBON BONDS; LIGNIN MODEL COMPOUNDS; MOLECULAR-OXYGEN; TRIPLE BOND; CATALYZED CLEAVAGE; AEROBIC OXIDATION; KETONES; ACID; DERIVATIVES;
D O I
10.1002/cssc.201501359
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A transition metal-free, chemoselective reaction was performed using the sodium tert-butoxide-oxygen ((NaOBu)-Bu-t-O-2) system, resulting in either oxidative dehomologation or direct oxidation of alcohols. In particular, the newly developed protocol may be used to predict the major product formed, which depends on alkyl chain length of the alcohols and reaction conditions. The rational mechanism of this transformation was also demonstrated by performing an O-18 isotopic labelling experiment. This protocol presents a straightforward method for biomass conversion of a lignin model compound to phenol and benzoic acid.
引用
收藏
页码:241 / 245
页数:5
相关论文
共 64 条
[1]  
[Anonymous], 2010, ANGEW CHEM
[2]   TOTAL SYNTHESIS OF (+/-)-QUADRONE [J].
BURKE, SD ;
MURTIASHAW, CW ;
SAUNDERS, JO ;
OPLINGER, JA ;
DIKE, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (16) :4558-4566
[3]   Studies on the Vanadium-Catalyzed Nonoxidative Depolymerization of Miscanthus giganteus-Derived Lignin [J].
Chan, Julian M. W. ;
Bauer, Stefan ;
Sorek, Hagit ;
Sreekumar, Sanil ;
Wang, Kun ;
Toste, F. Dean .
ACS CATALYSIS, 2013, 3 (06) :1369-1377
[4]   Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds [J].
Chen, Feng ;
Wang, Teng ;
Jiao, Ning .
CHEMICAL REVIEWS, 2014, 114 (17) :8613-8661
[5]  
Chen K., 2012, ANGEW CHEM, V124, P9989
[6]   Reductive Cleavage of the Csp2-Csp3 Bond of Secondary Benzyl Alcohols: Rhodium Catalysis Directed by N-Containing Groups [J].
Chen, Kang ;
Li, Hu ;
Lei, Zhi-Quan ;
Li, Yang ;
Ye, Wen-He ;
Zhang, Li-Sheng ;
Sun, Jian ;
Shi, Zhang-Jie .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) :9851-9855
[7]   Direct oxidative arylation via rhodium-catalyzed C-C bond cleavage of secondary alcohols with arylsilanes [J].
Chen, Kang ;
Li, Hu ;
Li, Yang ;
Zhang, Xi-Sha ;
Lei, Zhi-Quan ;
Shi, Zhang-Jie .
CHEMICAL SCIENCE, 2012, 3 (05) :1645-1649
[8]   THE ORGANOMETALLIC CHEMISTRY OF ALKANES [J].
CRABTREE, RH .
CHEMICAL REVIEWS, 1985, 85 (04) :245-269
[9]  
Dakin H.D., 1909, American Chemical Journal, V42, P477
[10]   A new ruthenium-catalyzed cleavage of a carbon-carbon triple bond: Efficient transformation of ethynyl alcohol into alkene and carbon monoxide [J].
Datta, S ;
Chang, CL ;
Yeh, KL ;
Liu, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9294-9295