B(C6F5)(3)-catalyzed hydrosilation of imines via silyliminium intermediates
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(C...
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Published in | Organic letters Vol. 2; no. 24; pp. 3921 - 3923 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
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WASHINGTON
Amer Chemical Soc
30.11.2000
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Abstract | 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. |
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AbstractList | 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. |
Author | Blackwell, JM Scoccitti, T Sonmor, ER Piers, WE |
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Keywords | ALCOHOLS BORON REDUCTION HYPERCOORDINATION ALDEHYDES CATIONS |
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References | LAMBERT, JB (WOS:A1994NR47800041) 1994; 13 Ishihara, K (WOS:000079164500001) 1999; 1999 Blackwell, JM (WOS:000081136200047) 1999; 64 LAMBERT, JB (WOS:A1995RN29500004) 1995; 95 Ooi, T (WOS:000074039100028) 1998; 120 Suwa, T (WOS:000085172400020) 1999; 1 Chen, EYX (WOS:000086603100008) 2000; 100 Kobayashi, S (WOS:000080452700002) 1999; 99 ISHIHARA, K (WOS:A1995RJ19400028) 1995; 68 Blackwell, JM (WOS:000085646500033) 2000; 2 GREENE TW (WOS:000165616300043.6) 1991 MACLEAN DB (WOS:000165616300043.15) 1986 LAMBERT, JB (WOS:A1992JB04600006) 1992 HUTCHINS RO (WOS:000165616300043.7) 1991; 8 Johannsen, M (WOS:000075346200030) 1998; 120 Parks, DJ (WOS:000087262500033) 2000; 65 Parks, DJ (WOS:A1996VK78000038) 1996; 118 Gevorgyan, V (WOS:000089338600041) 2000; 65 GEVORGYAN V (WOS:000165616300043.4) 1997 |
References_xml | – volume: 95 start-page: 1191 year: 1995 ident: WOS:A1995RN29500004 article-title: MODERN APPROACHES TO SILYLIUM CATIONS IN CONDENSED-PHASE publication-title: CHEMICAL REVIEWS contributor: fullname: LAMBERT, JB – year: 1991 ident: WOS:000165616300043.6 publication-title: PROTECIVE GROUPS ORG contributor: fullname: GREENE TW – volume: 8 start-page: 25 year: 1991 ident: WOS:000165616300043.7 publication-title: COMPREHENSIVE ORGANI contributor: fullname: HUTCHINS RO – start-page: 37 year: 1997 ident: WOS:000165616300043.4 publication-title: J CHEM SOC CHEM COMM contributor: fullname: GEVORGYAN V – volume: 13 start-page: 2430 year: 1994 ident: WOS:A1994NR47800041 article-title: SILYL CATIONS IN THE SOLID AND IN SOLUTION publication-title: ORGANOMETALLICS contributor: fullname: LAMBERT, JB – volume: 65 start-page: 6179 year: 2000 ident: WOS:000089338600041 article-title: A novel B(C6F5)(3)-catalyzed reduction of alcohols and cleavage of aryl and alkyl ethers with hydrosilanes publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo000726d contributor: fullname: Gevorgyan, V – start-page: 931 year: 1992 ident: WOS:A1992JB04600006 article-title: TRICOORDINATE TIN CATIONS IN SOLUTION UNDER AMBIENT CONDITIONS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: LAMBERT, JB – volume: 68 start-page: 1721 year: 1995 ident: WOS:A1995RJ19400028 article-title: TRIS(PENTAFLUOROPHENYL)BORON AS AN EFFICIENT, AIR-STABLE, AND WATER TOLERANT LEWIS-ACID CATALYST publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN contributor: fullname: ISHIHARA, K – volume: 120 start-page: 5327 year: 1998 ident: WOS:000074039100028 article-title: Hypercoordination of boron and aluminum: Synthetic utility as chelating Lewis acids publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Ooi, T – volume: 120 start-page: 7637 year: 1998 ident: WOS:000075346200030 article-title: Synthesis and application of the first chiral and highly Lewis acidic silyl cationic catalyst publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Johannsen, M – volume: 64 start-page: 4887 year: 1999 ident: WOS:000081136200047 article-title: B(C6F5)(3)-catalyzed silation of alcohols: A mild, general method for synthesis of silyl ethers publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Blackwell, JM – volume: 118 start-page: 9440 year: 1996 ident: WOS:A1996VK78000038 article-title: Tris(pentafluorophenyl)boron-catalyzed hydrosilation of aromatic aldehydes, ketones, and esters publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Parks, DJ – volume: 2 start-page: 695 year: 2000 ident: WOS:000085646500033 article-title: Mechanistic studies on selectivity in the B(C6F5)(3)-catalyzed allylstannation of aldehydes: Is hypercoordination at boron responsible? publication-title: ORGANIC LETTERS contributor: fullname: Blackwell, JM – volume: 1 start-page: 1579 year: 1999 ident: WOS:000085172400020 article-title: Synthesis of nitrogen heterocycles by intramolecular Michael type of amination via reduction of imines with di-n-butyliodotin hydride (n-Bu2SnIH) publication-title: ORGANIC LETTERS contributor: fullname: Suwa, T – volume: 1999 start-page: 527 year: 1999 ident: WOS:000079164500001 article-title: Arylboron compounds as acid catalysts in organic synthetic transformations publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Ishihara, K – volume: 100 start-page: 1391 year: 2000 ident: WOS:000086603100008 article-title: Cocatalysts for metal-catalyzed olefin polymerization: Activators, activation processes, and structure-activity relationships publication-title: CHEMICAL REVIEWS contributor: fullname: Chen, EYX – volume: 65 start-page: 3090 year: 2000 ident: WOS:000087262500033 article-title: Studies on the mechanism of B(C6F5)(3)-catalyzed hydrosilation of carbonyl functions publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Parks, DJ – start-page: 1608 year: 1986 ident: WOS:000165616300043.15 publication-title: J CHEM SOC CHEM COMM contributor: fullname: MACLEAN DB – volume: 99 start-page: 1069 year: 1999 ident: WOS:000080452700002 article-title: Catalytic enantioselective addition to imines publication-title: CHEMICAL REVIEWS contributor: fullname: Kobayashi, S |
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Snippet | A broad range of benzaldimines and ketimines can be hydrosilated efficiently, employing B(C6F5)(3) as a catalyst in conjunction with PhMe2SiH. Spectral... |
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Title | B(C6F5)(3)-catalyzed hydrosilation of imines via silyliminium intermediates |
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