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

来源：

CHEMSUSCHEM | 2016年 / 9卷 / 03期

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

页码：241 / 245

页数：5

共 64 条

[51] Copper-Catalyzed Aerobic Oxidative C-C Bond Cleavage for C-N Bond Formation: From Ketones to Amides [J].

Tang, Conghui ;

Jiao, Ning .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (25) :6528-6532

[52] Nickel-Catalyzed Regioselective Carbomagnesation of Methylenecyclopropanes through a Site-Selective Carbon-Carbon Bond Cleavage [J].

Terao, Jun ;

Tomita, Masahiro ;

Singh, Surya Prakash ;

Kambe, Nobuaki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (01) :144-147

[53] Recyclable Hypervalent Iodine(III) Reagent Iodosodilactone as an Efficient Coupling Reagent for Direct Esterification, Amidation, and Peptide Coupling [J].

Tian, Jun ;

Gao, Wen-Chao ;

Zhou, Dong-Mei ;

Zhang, Chi .

ORGANIC LETTERS, 2012, 14 (12) :3020-3023

[54] Catalytic reactions involving the cleavage of carbon-cyano and carbon-carbon triple bonds [J].

Tobisu, Mamoru ;

Chatani, Naoto .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (02) :300-307

[55] Rhodium(I)-Catalyzed Borylation of Nitriles through the Cleavage of Carbon-Cyano Bonds [J].

Tobisu, Mamoru ;

Kinuta, Hirotaka ;

Kita, Yusuke ;

Remond, Emmanuelle ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) :115-118

[56] Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: An organometallic ozonolysis [J].

Travis, BR ;

Narayan, RS ;

Borhan, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (15) :3824-3825

[57] Palladium-catalyzed cleavage reaction of carbon-carbon triple bond with molecular oxygen promoted by Lewis acid [J].

Wang, Azhong ;

Jiang, Huanfeng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (15) :5030-+

[58] AIBN-Catalyzed Oxidative Cleavage of gem-Disubstituted Alkenes with O2 as an Oxidant [J].

Wang, Guang-Zu ;

Li, Xing-Long ;

Dai, Jian-Jun ;

Xu, Hua-Jian .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (15) :7220-7225

[59] Highly Regioselective Synthesis of 1,3-Diiodonaphthalene Derivatives via a Sequential Cascade Iodocyclization [J].

Wang, Li-Jing ;

Zhu, Hai-Tao ;

Lu, Lei ;

Yang, Fang ;

Liu, Xue-Yuan ;

Liang, Yong-Min .

ORGANIC LETTERS, 2012, 14 (08) :1990-1993

[60] Efficient ''dehomologation'' of di-O-isopropylidenehexofuranose derivatives to give O-isopropylidenepentofuranoses by sequential treatment with periodic acid in ethyl acetate and sodium borohydride [J].

Xie, MQ ;

Berges, DA ;

Robins, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :5178-5179

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