Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates

被引：70

作者：

Ng, Sze-Sze ^{[1
]}

Ho, Chun-Yu ^{[1
]}

Jamison, Timothy F. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 35期

关键词：

D O I：

10.1021/ja062866w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A full account of two recently developed nickel-catalyzed coupling reactions of alkenes, aldehydes, and silyl triflates is presented. These reactions provide either allylic alcohol or homoallylic alcohol derivatives selectively, depending on the ligand employed. These processes are believed to be mechanistically distinct from Lewis acid-catalyzed carbonyl-ene reactions, and several lines of evidence supporting this hypothesis are discussed.

引用

收藏

页码：11513 / 11528

页数：16

相关论文

共 98 条

[1] Scandium trifluoromethanesulfonate, an efficient catalyst for the intermolecular carbonyl-ene reaction and the intramolecular cyclisation of citronellal. [J].

Aggarwal, VK ;

Vennall, GP ;

Davey, PN ;

Newman, C .

TETRAHEDRON LETTERS, 1998, 39 (14) :1997-2000

[2] Synthesis of a tricyclic mescaline analogue by catalytic C-H bond activation [J].

Ahrendt, KA ;

Bergman, RG ;

Ellman, JA .

ORGANIC LETTERS, 2003, 5 (08) :1301-1303

[3] Helical chirality control of palladium complexes that bear a tetrakis(phosphanyl)terphenyl ligand: Application as asymmetric Lewis acid catalysts [J].

Aikawa, K ;

Mikami, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5458-5461

[4] Absorption of maleic acid-anhydride and azodicarbon acid-ester in simple unsaturated carbohydrogens. Information on the substitution processes in the allyl position. [J].

Alder, K ;

Pascher, F ;

Schmitz, A .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1943, 76 :27-53

[5] INTRAMOLECULAR OLEFINIC ALDEHYDE PRINS REACTIONS FOR THE CONSTRUCTION OF 5-MEMBERED RINGS [J].

ANDERSEN, NH ;

HADLEY, SW ;

KELLY, JD ;

BACON, ER .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) :4144-4151

[6] Palladium-indium mediated Barbier-type allylation of aldehydes with allenes [J].

Anwar, U ;

Grigg, R ;

Rasparini, M ;

Savic, V ;

Sridharan, V .

CHEMICAL COMMUNICATIONS, 2000, (08) :645-646

[7] Ferrocenyl monophosphine ligands: Synthesis and applications in the Suzuki-Miyaura coupling of aryl chlorides [J].

Baillie, C ;

Zhang, LX ;

Xiao, JL .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) :7779-7782

[8] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[9]

Blom R., 2001, ORGANOMETALLIC CATAL, DOI DOI 10.1007/978-3-642-59465-6

[10] Metal-catalyzed di-tert-butylsilylene transfer:: Synthesis and reactivity of silacyclopropanes [J].

Cirakovic, J ;

Driver, TG ;

Woerpel, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (12) :4007-4012

← 1 2 3 4 5 6 7 8 9 10 →