Efficient activation of 2-Iminomethylpyridine/Cobalt-Based alkyne [2+2+2}cycloaddition catalyst by addition of a silver salt

被引：56

作者：

Goswami, Avijit ^{[1
]}

Itoa, Taichi ^{[1
]}

Okamoto, Sentaro ^{[1
]}

机构：

[1] Kanagawa Univ, Dept Mat & Life Chem, Kanagawa Ku, Yokohama, Kanagawa 2218686, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 14-15期

关键词：

catalytic cycloaddition; cobalt; iminomethylpyridine; silver triflate; substituted benzenes;

D O I：

10.1002/adsc.200700188

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The addition of silver triflate (AgOTf) or silver hexafluoroantimonate (AgSbF6) significantly increased the activity of the 2-(arylimino)methyl-pyridine/cobalt(II) chloride hexahydrate (COCl2 center dot 6H(2)O)/zinc catalyst in alkyne cyclotrimerizations thereby accelerating the reaction and enabling the use of unactivated, simple internal alkynes as the monoyne substrate: The rate of reaction was found to be highly dependent on the nature of the counter anion (X-) and the ligand (L) in the postulated cationic cobalt(I) complex [LCo(l)]X-+(-).

引用

页码：2368 / 2374

页数：7

共 48 条

[1] Novel [2+2+1] cyclotrimerization of alkynes mediated by bidentate cyclopentadienyl-phosphine ruthenium complexes [J].

Becker, E ;

Mereiter, K ;

Puchberger, M ;

Schmid, R ;

Kirchner, K .

ORGANOMETALLICS, 2003, 22 (15) :3164-3170

[2] Bis-alkoxycarbonylation of styrene by pyridinimine palladium catalysts [J].

Bianchini, C ;

Lee, HM ;

Mantovani, G ;

Meli, A ;

Oberhauser, W .

NEW JOURNAL OF CHEMISTRY, 2002, 26 (04) :387-397

[3] The role of bulky substituents in the polymerization of ethylene using late transition metal catalysts: a comparative study of nickel and iron catalyst systems [J].

Britovsek, GJP ;

Baugh, SPD ;

Hoarau, O ;

Gibson, VC ;

Wass, DF ;

White, AJP ;

Williams, DJ .

INORGANICA CHIMICA ACTA, 2003, 345 :279-291

[4] PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].

BURK, MJ ;

FEASTER, JE ;

NUGENT, WA ;

HARLOW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138

[5] [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].

Chopade, Pramod R. ;

Louie, Janis .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327

[6] Rhodium-catalyzed synthesis of eight-membered rings [J].

DeBoef, Brenton ;

Counts, W. Richard ;

Gilbertson, Scott R. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) :799-804

[7] C-2-SYMMETRIC CATIONIC COPPER(II) COMPLEXES AS CHIRAL LEWIS-ACIDS - COUNTERION EFFECTS IN THE ENANTIOSELECTIVE DIELS-ALDER REACTION [J].

EVANS, DA ;

MURRY, JA ;

VONMATT, P ;

NORCROSS, RD ;

MILLER, SJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :798-800

[8] Cycloadditions, cycloisomerizations and related reactions of alkynes bearing group 13 or 14 heteroelements [J].

Gandon, V ;

Aubert, C ;

Malacria, M .

CURRENT ORGANIC CHEMISTRY, 2005, 9 (17) :1699-1712

[9] Recent progress in cobalt-mediated [2+2+2] cycloaddition reactions [J].

Gandon, Vincent ;

Aubert, Corinne ;

Malacria, Max .

CHEMICAL COMMUNICATIONS, 2006, (21) :2209-2217

[10] Palladium-catalyzed highly chemo- and regioselective formal [2+2+2] sequential cycloaddition of alkynes: A renaissance of the well known trimerization reaction? [J].

Gevorgyan, V ;

Radhakrishnan, U ;

Takeda, A ;

Rubina, M ;

Rubin, M ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2835-2841

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