Copper-catalyzed silylation of p-quinone methides: new entry to dibenzylic silanes

被引：90

作者：

Lopez, Aurora ^{[1
]}

Parra, Alejandro ^{[1
]}

Jarava-Barrera, Carlos ^{[1
]}

Tortosa, Mariola ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 100期

基金：

欧洲研究理事会;

关键词：

B BOND ACTIVATION; C-SI BOND; NUCLEOPHILIC SILICON; STABILIZED CARBANIONS; ALLYLIC SUBSTITUTION; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITIONS; UNIQUE BEHAVIOR; ALDEHYDES; DERIVATIVES;

D O I：

10.1039/c5cc06653k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient and general copper(I)-catalyzed silylation of p-quinone-methides is described. Non-symmetric dibenzylic silanes are obtained in high yields under mild reaction conditions. These compounds can be used as bench-stable benzylic carbanion precursors.

引用

页码：17684 / 17687

页数：4

共 69 条

[1] Nucleophilicity Parameters of Pyridinium Ylides and Their Use in Mechanistic Analyses [J].

Allgaeuer, Dominik S. ;

Mayer, Peter ;

Mayr, Herbert .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (40) :15216-15224

[2] PARA-QUINONE METHIDE INITIATED CYCLIZATION REACTIONS [J].

ANGLE, SR ;

TURNBULL, KD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1136-1138

[3]

[Anonymous], 1974, CHEM QUINONOID COMPO

[4] Nucleophilicity Parameters for Phosphoryi-Stabilized Carbanions and Phosphorus Ylides: Implications for Wittig and Related Olefination Reactions [J].

Appel, Roland ;

Loos, Robert ;

Mayr, Herbert .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) :704-714

[5]

Bains W, 2003, CURR OPIN DRUG DISC, V6, P526

[6] HIGHLY CHEMOSELECTIVE ADDITION OF (ORTHO-NITROBENZYL)SILANES TO NONENOLIZABLE ALDEHYDES [J].

BARTOLI, G ;

BOSCO, M ;

CARETTI, D ;

DALPOZZO, R ;

TODESCO, PE .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4381-4384

[7] A NEW ORGANOSILICIATED SYNTONE - BENZYLTRIMETHYLSILANE [J].

BENNETAU, B ;

DUNOGUES, J .

TETRAHEDRON LETTERS, 1983, 24 (39) :4217-4218

[8] Inverse solvent effects in carbocation carbanion combination reactions: The unique behavior of trifluoromethylsulfonyl stabilized carbanions [J].

Berger, Stefan T. A. ;

Ofial, Armin R. ;

Mayr, Herbert .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (31) :9753-9761

[9] Nucleophilic reactivities of carbanions in water: The unique behavior of the malodinitrile anion [J].

Bug, T ;

Mayr, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12980-12986

[10] The Emergence of Quinone Methides in Asymmetric Organocatalysis [J].

Caruana, Lorenzo ;

Fochi, Mariafrancesca ;

Bernardi, Luca .

MOLECULES, 2015, 20 (07) :11733-11764

← 1 2 3 4 5 6 7 →