B(C6F5)3-catalyzed hydrosilation of imines via silyliminium intermediates

被引：307

作者：

Blackwell, JM ^{[1
]}

Sonmor, ER ^{[1
]}

Scoccitti, T ^{[1
]}

Piers, WE ^{[1
]}

机构：

[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 24期

关键词：

D O I：

10.1021/ol006695q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A broad range of benzaldimines and ketimines can be hydrosilated efficiently, employing B(C6F5)(3) as a catalyst in conjunction with PhMe2SiH. Spectral evidence supports the intermediacy of a silyliminium cation with a hydridoborate counterion formed via abstraction of a hydride from PhMe2SiH by B(C6F5)(3) in the presence of imines.

引用

页码：3921 / 3923

页数：3

共 19 条

[1] Mechanistic studies on selectivity in the B(C6F5)3-catalyzed allylstannation of aldehydes:: Is hypercoordination at boron responsible? [J].

Blackwell, JM ;

Piers, WE ;

Parvez, M .

ORGANIC LETTERS, 2000, 2 (05) :695-698

[2] B(C6F5)3-catalyzed silation of alcohols:: A mild, general method for synthesis of silyl ethers [J].

Blackwell, JM ;

Foster, KL ;

Beck, VH ;

Piers, WE .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4887-4892

[3] Cocatalysts for metal-catalyzed olefin polymerization: Activators, activation processes, and structure-activity relationships [J].

Chen, EYX ;

Marks, TJ .

CHEMICAL REVIEWS, 2000, 100 (04) :1391-1434

[4] A novel B(C6F5)3-catalyzed reduction of alcohols and cleavage of aryl and alkyl ethers with hydrosilanes [J].

Gevorgyan, V ;

Rubin, M ;

Benson, S ;

Liu, JX ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6179-6186

[5]

GEVORGYAN V, 1997, J CHEM SOC CHEM COMM, P37

[6]

GREENE TW, 1991, PROTECIVE GROUPS ORG

[7]

Hutchins R. O., 1991, Comprehensive Organic Synthesis, V8, P25, DOI DOI 10.1016/B978-0-08-052349-1.00218-3

[8]

Ishihara K, 1999, EUR J ORG CHEM, V1999, P527

[9] TRIS(PENTAFLUOROPHENYL)BORON AS AN EFFICIENT, AIR-STABLE, AND WATER TOLERANT LEWIS-ACID CATALYST [J].

ISHIHARA, K ;

HANAKI, N ;

FUNAHASHI, M ;

MIYATA, M ;

YAMAMOTO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (06) :1721-1730

[10] Synthesis and application of the first chiral and highly Lewis acidic silyl cationic catalyst [J].

Johannsen, M ;

Jorgensen, KA ;

Helmchen, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7637-7638

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