Novel Addition and [3+2] Cycloaddition Reactions of Stannyl- and Silyl-ortho-carboranes to Carbonyl Compounds

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Title:Novel Addition and [3+2] Cycloaddition Reactions of Stannyl- and Silyl-ortho-carboranes to Carbonyl Compounds
Creators:
Nakamura, Hiroyuki
Yamamoto, Yoshinori
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 5, pp. 829-846
Uncontrolled Keywords:[3+2] Annulations, Carbonyl compounds, Palladium catalysis, Stannanes, Silanes, Carboranes, Additions, Boron neutron capture therapy, <i>ortho</i>-Carborane

Abstract

Stannyl- and silyl-<i>ortho</i>-carboranes serve as an <i>ortho</i>-carborane carbanion equivalents in the addition reaction to aldehydes. The reaction of (tributylstannyl)-<i>ortho</i>-carborane <strong>2</strong> with aldehydes <strong>4</strong> in the presence of palladium(0) catalysts gave the corresponding (<i>ortho</i>-carboranyl) carbinols <strong>5</strong> in good to high yields. The reaction of (trimethylsilyl)-<i>ortho</i>-carborane <strong>3</strong> with aldehydes <strong>4</strong> in the presence of tetrabutylammonium fluoride (TBAF) gave the corresponding (<i>ortho</i>-carboranyl) carbinols <strong>5</strong> in high yields. Furthermore, (trimethylsilyl)-<i>ortho</i>-carborane <strong>3</strong> underwent a facile [3+2] annulation reaction with various α,β-unsaturated enals and enones in the presence of tetrabutylammonium fluoride, giving the corresponding five-membered carboracyclic products <strong>14</strong> in good to high yields.

Title:Novel Addition and [3+2] Cycloaddition Reactions of Stannyl- and Silyl-ortho-carboranes to Carbonyl Compounds
Creators:
Nakamura, Hiroyuki
Yamamoto, Yoshinori
Uncontrolled Keywords:[3+2] Annulations, Carbonyl compounds, Palladium catalysis, Stannanes, Silanes, Carboranes, Additions, Boron neutron capture therapy, <i>ortho</i>-Carborane
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:5
Page Range:pp. 829-846
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990829UNSPECIFIED
ID Code:1520
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:10

Citation

Nakamura, Hiroyuki; Yamamoto, Yoshinori (1999) Novel Addition and [3+2] Cycloaddition Reactions of Stannyl- and Silyl-ortho-carboranes to Carbonyl Compounds. Collection of Czechoslovak Chemical Communications, 64 (5). pp. 829-846. ISSN 0010-0765

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