Benzylation of Nitroalkanes Using Copper-Catalyzed Thermal Redox Catalysis: Toward the Facile C-Alkylation of Nitroalkanes

被引：56

作者：

Gildner, Peter G. ^{[1
]}

Gietter, Amber A. S. ^{[1
]}

Cui, Di ^{[1
]}

Watson, Donald A. ^{[1
]}

机构：

[1] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 24期

关键词：

QUATERNARY CARBON CENTERS; NITRO-COMPOUNDS; ASYMMETRIC ALKYLATION; POLYMERIZATION; SUBSTITUTION; ALLYLATION; COMPLEXES; NITRATES; ANIONS;

D O I：

10.1021/ja304561c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The C-alkylation of nitroalkanes under mild conditions has been a significant challenge in organic synthesis for more than a century. Herein we report a simple Cu(I) catalyst, generated in situ, that is highly effective for C-benzylation of nitroalkanes using abundant benzyl bromides and related heteroaromatic compounds. This process, which we believe proceeds via a thermal redox mechanism, allows access to a variety of complex nitroalkanes under mild reaction conditions and represents the first step toward the development of a general catalytic system for the alkylation of nitroalkanes.

引用

页码：9942 / 9945

页数：4

共 47 条

[1] PALLADIUM CATALYZED C-ALLYLATION OF NITROALKANES [J].

ALEKSANDROWICZ, P ;

PIOTROWSKA, H ;

SAS, W .

TETRAHEDRON, 1982, 38 (09) :1321-1327

[2] Substituted acyclic sulfonamides as human cannabinoid-1 receptor inverse agonists [J].

Armstrong, Helen E. ;

Galka, Amy ;

Lin, Linus S. ;

Lanza, Thomas J., Jr. ;

Jewell, James P. ;

Shah, Shrenik K. ;

Guthikonda, Ravi ;

Truong, Quang ;

Chang, Linda L. ;

Quaker, Grace ;

Colandrea, Vincent J. ;

Tong, Xinchun ;

Wang, Junying ;

Xu, Sherry ;

Fong, Tung M. ;

Shen, Chun-Pyn ;

Lao, Julie ;

Chen, Jing ;

Shearman, Lauren P. ;

Stribling, D. Sloan ;

Rosko, Kimberly ;

Strack, Alison ;

Ha, Sookhee ;

Van der Ploeg, Lex ;

Goulet, Mark T. ;

Hagmann, William K. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (08) :2184-2187

[3]

BRANCHAUD BP, 1988, TETRAHEDRON LETT, V29, P6545

[4] Salts of nitro compounds II The reaction of the silver salt of phenylnitromethane with diphenylbromomethane [J].

Brown, GB ;

Shriner, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1937, 2 (04) :376-380

[5] Atom transfer radical cyclisation reactions mediated by copper complexes [J].

Clark, AJ .

CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) :1-11

[6] Stereoselective formation of quaternary carbon centers and related functions [J].

Denissova, I ;

Barriault, L .

TETRAHEDRON, 2003, 59 (51) :10105-10146

[7] Cobalt-catalyzed cross-coupling reactions [J].

Gosmini, Corinne ;

Begouin, Jeanne-Marie ;

Moncomble, Aurelien .

CHEMICAL COMMUNICATIONS, 2008, (28) :3221-3233

[8] THE REACTION OF BENZYL HALIDES WITH THE SODIUM SALT OF 2-NITROPROPANE - A GENERAL SYNTHESIS OF SUBSTITUTED BENZALDEHYDES [J].

HASS, HB ;

BENDER, ML .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (05) :1767-1769

[9] Pharmacokinetics and pharmacodynamic effects of the oral DPP-4 inhibitor sitagliptin in middle-aged obese subjects [J].

Herman, Gary A. ;

Bergman, Arthur ;

Liu, Fang ;

Stevens, Cathy ;

Wang, Amy Q. ;

Zeng, Wei ;

Chen, Li ;

Snyder, Karen ;

Hilliard, Deborah ;

Tanen, Michael ;

Tanaka, Wesley ;

Meehan, Alan G. ;

Lasseter, Kenneth ;

Dilzer, Stacy ;

Blum, Robert ;

Wagner, John A. .

JOURNAL OF CLINICAL PHARMACOLOGY, 2006, 46 (08) :876-886

[10] Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners [J].

Jana, Ranjan ;

Pathak, Tejas P. ;

Sigman, Matthew S. .

CHEMICAL REVIEWS, 2011, 111 (03) :1417-1492

← 1 2 3 4 5 →