Metal-catalyzed synthesis of hetero-substituted alkenes and alkynes

被引：74

作者：

Evano, Gwilherm ^{[1
]}

Gaumont, Annie-Claude ^{[2
,3
]}

Alayrac, Carole ^{[2
,3
]}

Wrona, Iwona E. ^{[4
]}

Giguere, Joshua R. ^{[5
]}

Delacroix, Olivier ^{[2
,3
]}

Bayle, Alexandre ^{[6
]}

Jouvin, Kevin ^{[6
]}

Theunissen, Cedric ^{[1
]}

Gatignol, Jeremie ^{[2
,3
]}

Silvanus, Andrew C. ^{[6
]}

机构：

[1] Univ Libre Bruxelles, Lab Chim Organ, Serv Chim & Physicochim Organ, Ave FD Roosevelt 50,CP160-06, B-1050 Brussels, Belgium

[2] ENSICAEN, Lab Chim Mol & Thioorgan, CNRS, UMR 6507,INC3M,FR3038, F-14050 Caen, France

[3] Univ Caen Basse Normandie, F-14050 Caen, France

[4] Cubist Pharmaceut, Discovery Chem, Lexington, MA 02421 USA

[5] Rhodes Technol, Proc R&D, Coventry, RI 02816 USA

[6] Univ Versailles St Quentin Yvelines, Inst Lavoisier Versailles, CNRS, UMR 8180, F-78035 Versailles, France

来源：

TETRAHEDRON | 2014年 / 70卷 / 08期

关键词：

Alkenylphosphonates; Alkenylphosphines; Alkenylphosphine oxides; Alkynylphosphonates; Alkynylphosphines; Alkynylphosphine oxides; Catalysis; Enamines; Enamides; Enol ethers; Metal-catalyzed reactions; Silyl enol ethers; Ynamides; Ynol ethers; CROSS-COUPLING REACTION; ANTI-MARKOVNIKOV-ADDITION; HIGHLY SELECTIVE ISOMERIZATION; VINYLIC SUBSTITUTION-REACTIONS; AEROBIC OXIDATIVE AMINATION; ELECTRON-RICH OLEFINS; CARBON BOND FORMATION; SILYL ENOL ETHERS; ONE-POT SYNTHESIS; OPENING/CROSS-METATHESIS REACTIONS;

D O I：

10.1016/j.tet.2013.11.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[No abstract available]

引用

页码：1529 / 1616

页数：88

共 567 条

[1] An improved procedure for the synthesis of vinylphosphonate-linked nucleic acids [J].

Abbas, S ;

Hayes, CJ .

TETRAHEDRON LETTERS, 2000, 41 (22) :4513-4517

[2] Commercially available 5′-DMT phosphoramidites as reagents for the synthesis of vinylphosphonate-linked oligonucleic acids [J].

Abbas, S ;

Bertram, RD ;

Hayes, CJ .

ORGANIC LETTERS, 2001, 3 (21) :3365-3367

[3] Neutral copper-phosphido-borane complexes: synthesis, characterization, and use as precatalysts in Csp-P bond formation [J].

Abdellah, Ibrahim ;

Bernoud, Elise ;

Lohier, Jean-Francois ;

Alayrac, Carole ;

Toupet, Loic ;

Lepetit, Christine ;

Gaumont, Annie-Claude .

CHEMICAL COMMUNICATIONS, 2012, 48 (34) :4088-4090

[4] Annulation of internal alkynes through a hydroamination/aza-Heck reaction sequence for the regioselective synthesis of indoles [J].

Ackermann, Lutz ;

Sandmann, Rene ;

Villar, Amparo ;

Kaspar, Ludwig T. .

TETRAHEDRON, 2008, 64 (05) :769-777

[5] A convenient and direct route to phosphinoalkynes via copper-catalyzed cross-coupling of terminal alkynes with chlorophosphanes [J].

Afanasiev, VV ;

Beletskaya, IP ;

Kazankova, MA ;

Efimova, IV ;

Antipin, MU .

SYNTHESIS-STUTTGART, 2003, (18) :2835-2838

[6] Convenient and direct preparation of tertiary phosphines via nickel-catalysed cross-coupling [J].

Ager, DJ ;

East, MB ;

Eisenstadt, A ;

Laneman, SA .

CHEMICAL COMMUNICATIONS, 1997, (24) :2359-2360

[7] A new method for the preparation of silyl enol ethers from carbonyl compounds and (Trimethylsilyl)diazomethane in a regiospecific and highly stereoselective manner [J].

Aggarwal, VK ;

Sheldon, CG ;

Macdonald, GJ ;

Martin, WP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) :10300-10301

[8] FACILE ROUTE TO 1-PHOSPHORYL-1,3-DIENES AND 1-SULFONYL-1,3-DIENES VIA PALLADIUM-CATALYZED ELIMINATION OF ALLYLIC ACETATES [J].

AKERMARK, B ;

NYSTROM, JE ;

REIN, T ;

BACKVALL, JE ;

HELQUIST, P ;

ASLANIAN, R .

TETRAHEDRON LETTERS, 1984, 25 (50) :5719-5722

[9] Synthesis of diethyl 2-(aryl) vinylphosphonates by the Heck reaction catalysed by well-defined palladium complexes [J].

Al-Maksoud, Walid ;

Mesnager, Julien ;

Jaber, Farouk ;

Pinel, Catherine ;

Djakovitch, Laurent .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (20) :3222-3231

[10]

Al-Shboul T. M. A., 2011, J ORGANOMET CHEM, V696, P216

← 1 2 3 4 5 6 7 8 9 10 →