Construction of tetrasubstituted carbon by an organocatalyst: Cyanation reaction of ketones and ketimines catalyzed by a nucleophilic N-heterocyclic carbene

被引：50

作者：

Fukuda, Yoshimasa ^{[1
]}

Kondo, Kazuhiro ^{[1
]}

Aoyama, Toyohiko ^{[1
]}

机构：

[1] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan

来源：

SYNTHESIS-STUTTGART | 2006年 / 16期

关键词：

N-heterocyclic carbene; tetrasubstituted carbon; nucleophilic organocatalyst; cyanation; trimethylsilyl cyanide;

D O I：

10.1055/s-2006-942483

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for cyanation reaction of ketones and ketimines having lower reactivity than aldehydes and aldimines with TMSCN in the presence of N-heterocyclic carbene prepared from 1,3-bis(2,4,6-trimetbylphenyl)imidazolium chloride and potassium tert-butoxide, as a nucleophilic organocatalyst, is described. These cyanations of ketones and ketimines afford the corresponding products in good yields under mild reaction conditions.

引用

页码：2649 / 2652

页数：4

共 28 条

[1] Solvent-free synthesis of cyanohydrin derivatives catalysed by triethylamine [J].

Baeza, A ;

Nájera, C ;

Retamosa, MD ;

Sansano, JM .

SYNTHESIS-STUTTGART, 2005, (16) :2787-2797

[2] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].

Burstein, C ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208

[3] Enantioselective cyanosilylation of ketones catalyzed by double-activation catalysts with N-oxides [J].

Chen, FX ;

Qin, B ;

Feng, XM ;

Zhang, GL ;

Jiang, YZ .

TETRAHEDRON, 2004, 60 (46) :10449-10460

[4] First example of N-heterocyclic carbenes as catalysts for living polymerization:: Organocatalytic ring-opening polymerization of cyclic esters [J].

Connor, EF ;

Nyce, GW ;

Myers, M ;

Möck, A ;

Hedrick, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) :914-915

[5] P(RNCH2CH2)N:: efficient catalysts for the cyanosilylation of aldehydes and ketones [J].

Fetterly, BM ;

Verkade, JG .

TETRAHEDRON LETTERS, 2005, 46 (46) :8061-8066

[6] Umpolung of Michael acceptors catalyzed by N-heterocyclic carbenes [J].

Fischer, C ;

Smith, SW ;

Powell, DA ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1472-1473

[7] Cyano-phosphorylation of aldehydes catalyzed by a nucleophilic N-heterocyclic carbene [J].

Fukuda, Y ;

Maeda, Y ;

Kondo, K ;

Aoyama, T .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (03) :397-398

[8] An N-heterocyclic carbene as a nucleophilic catalyst for cyanosilylation of aldehydes [J].

Fukuda, Y ;

Maeda, Y ;

Ishii, S ;

Kondo, K ;

Aoyama, T .

SYNTHESIS-STUTTGART, 2006, (04) :589-590

[9] Strecker reaction of aldimines catalyzed by a nucleophilic N-heterocyclic carbene [J].

Fukuda, Yoshimasa ;

Maeda, Yuka ;

Kondo, Kazuhiro ;

Aoyama, Toyohiko .

SYNTHESIS-STUTTGART, 2006, 12 (12) :1937-1939

[10] Transesterification/acylation reactions catalyzed by molecular catalysts [J].

Grasa, GA ;

Singh, R ;

Nolan, SP .

SYNTHESIS-STUTTGART, 2004, (07) :971-985

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