Site-Selectivity Control in Organic Reactions: A Quest To Differentiate Reactivity among the Same Kind of Functional Groups

被引：143

作者：

Huang, Zhongxing ^{[1
]}

Dong, Guangbin ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, 5735 South Ellis Ave, Chicago, IL 60637 USA

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2017年 / 50卷 / 03期

关键词：

C-H BONDS; BETA-ARYLATION; CATALYSTS; KETONES;

D O I：

10.1021/acs.accounts.6b00476

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

On our path to the perfection of organic synthesis lies the challenge of controlling site selectivity, which is the differentiation of reactivity among the same kind of functional groups. Overcoming this challenge would significantly enhance synthetic efficiency and minimize waste production, which in turn calls for the development of new catalysts, reagents, tactics, and innovative strategies.

引用

页码：465 / 471

页数：7

共 22 条

[1] STUDIES ON SULFOCHLORINATION OF PARAFFINS .9. REGULARITIES OF THE SULFOCHLORINATION OF BRANCHED-CHAIN PARAFFINS [J].

ESTEL, D ;

MATEEW, K ;

PRITZKOW, W ;

SCHMIDTRENNER, W .

JOURNAL FUR PRAKTISCHE CHEMIE, 1981, 323 (02) :262-268

[2] Highly active and selective catalysts for the formation of α-aryl ketones [J].

Fox, JM ;

Huang, XH ;

Chieffi, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1360-1370

[3] Catalyst-Controlled Aliphatic C-H Oxidations with a Predictive Model for Site-Selectivity [J].

Gormisky, Paul E. ;

White, M. Christina .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (38) :14052-14055

[4] A peptide-based catalyst approach to regioselective functionalization of carbohydrates [J].

Griswold, KS ;

Miller, SJ .

TETRAHEDRON, 2003, 59 (45) :8869-8875

[5] Catalytic Direct β-Arylation of Simple Ketones with Aryl Iodides [J].

Huang, Zhongxing ;

Dong, Guangbin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (47) :17747-17750

[6] CATALYTIC-HYDROGENATION OF 7-METHYLBICYCLO[3.3.1]NON-6-EN-3-ONE - ANOMALOUSLY HIGH SELECTIVITIES ON PD AND CO BLACK CATALYSTS [J].

ISHIYAMA, J ;

SENDA, Y ;

IMAIZUMI, S .

CHEMISTRY LETTERS, 1983, (08) :1243-1244

[7] Metal-Catalyzed α-Arylation of Carbonyl and Related Molecules: Novel Trends in C-C Bond Formation by C-H Bond Functionalization [J].

Johansson, Carin C. C. ;

Colacot, Thomas J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (04) :676-707

[8] A catalytic one-step process for the chemo- and regioselective acylation of Monosaccharides [J].

Kawabata, Takeo ;

Muramatsu, Wataru ;

Nishio, Tadashi ;

Shibata, Takeshi ;

Schedel, Hartmut .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) :12890-12895

[9] Borinic Acid-Catalyzed Regioselective Acylation of Carbohydrate Derivatives [J].

Lee, Doris ;

Taylor, Mark S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (11) :3724-3727

[10] Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts [J].

Lewis, Chad A. ;

Miller, Scott J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (34) :5616-5619

← 1 2 3 →