Cyclization/Hydrosilylation of Functionalized 1,6-Diynes Catalyzed by Cationic Platinum Complexes Containing Bidentate Nitrogen Ligands
A 1:1 mixture of the platinum dimethyl diimine complex [PhNC(Me)C(Me)NPh]PtMe2 (4a) and B(C6F5)3 catalyzed the cyclization/hydrosilylation of dimethyl dipropargylmalonate (1) and HSiEt3 to form 1,1-dicarbomethoxy-3-methylene-4-(triethylsilylmethylene)cyclopentane (3) in 82% isolated yield with 26:...
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| Published in | Journal of organic chemistry Vol. 67; no. 9; pp. 2778 - 2788 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
03.05.2002
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0022-3263 1520-6904 |
| DOI | 10.1021/jo015986p |
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| Abstract | A 1:1 mixture of the platinum dimethyl diimine complex [PhNC(Me)C(Me)NPh]PtMe2 (4a) and B(C6F5)3 catalyzed the cyclization/hydrosilylation of dimethyl dipropargylmalonate (1) and HSiEt3 to form 1,1-dicarbomethoxy-3-methylene-4-(triethylsilylmethylene)cyclopentane (3) in 82% isolated yield with 26:1 Z:E selectivity. Platinum-catalyzed diyne cyclization/hydrosilylation tolerated a range of functional groups including esters, sulfones, acetals, silyl ethers, amides, and hindered ketones. Diynes that possessed propargylic substitution underwent facile cyclization/hydrosilylation to form silylated 1,2-dialkylidene cyclopentanes as mixtures of regioisomers. Diynes that possessed an electron-deficient internal alkyne underwent cyclization/hydrosilylation in moderate yield to form products resulting from silyl transfer to the less substituted alkyne. The silylated 1,2-dialkylidenecyclopentanes formed via diyne cyclization/hydrosilylation underwent a range of transformations including protodesilylation, Z/E isomerization, and [4 + 2] cycloaddition with dieneophiles. |
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| AbstractList | A 1:1 mixture of the platinum dimethyl diimine complex [PhN[double bond]C(Me)C(Me)[double bond]NPh]PtMe(2) (4a) and B(C(6)F(5))(3) catalyzed the cyclization/hydrosilylation of dimethyl dipropargylmalonate (1) and HSiEt(3) to form 1,1-dicarbomethoxy-3-methylene-4-(triethylsilylmethylene)cyclopentane (3) in 82% isolated yield with 26:1 Z:E selectivity. Platinum-catalyzed diyne cyclization/hydrosilylation tolerated a range of functional groups including esters, sulfones, acetals, silyl ethers, amides, and hindered ketones. Diynes that possessed propargylic substitution underwent facile cyclization/hydrosilylation to form silylated 1,2-dialkylidene cyclopentanes as mixtures of regioisomers. Diynes that possessed an electron-deficient internal alkyne underwent cyclization/hydrosilylation in moderate yield to form products resulting from silyl transfer to the less substituted alkyne. The silylated 1,2-dialkylidenecyclopentanes formed via diyne cyclization/hydrosilylation underwent a range of transformations including protodesilylation, Z/E isomerization, and [4 + 2] cycloaddition with dieneophiles.A 1:1 mixture of the platinum dimethyl diimine complex [PhN[double bond]C(Me)C(Me)[double bond]NPh]PtMe(2) (4a) and B(C(6)F(5))(3) catalyzed the cyclization/hydrosilylation of dimethyl dipropargylmalonate (1) and HSiEt(3) to form 1,1-dicarbomethoxy-3-methylene-4-(triethylsilylmethylene)cyclopentane (3) in 82% isolated yield with 26:1 Z:E selectivity. Platinum-catalyzed diyne cyclization/hydrosilylation tolerated a range of functional groups including esters, sulfones, acetals, silyl ethers, amides, and hindered ketones. Diynes that possessed propargylic substitution underwent facile cyclization/hydrosilylation to form silylated 1,2-dialkylidene cyclopentanes as mixtures of regioisomers. Diynes that possessed an electron-deficient internal alkyne underwent cyclization/hydrosilylation in moderate yield to form products resulting from silyl transfer to the less substituted alkyne. The silylated 1,2-dialkylidenecyclopentanes formed via diyne cyclization/hydrosilylation underwent a range of transformations including protodesilylation, Z/E isomerization, and [4 + 2] cycloaddition with dieneophiles. A 1:1 mixture of the platinum dimethyl diimine complex [PhNT=C(,Me)C(Me)=NPh]PtMe2 (4a) and B(C6F5)(3) catalyzed the cyclization/hydrosilylation of dimethyl dipropargylmalonate (1) and HSiEt3 to form 1,1-dicarbomethoxy-3-methylene-4-(triethylsilylmethylene)cyclopentane (3) in 82% isolated yield,with 26:1 Z:E selectivity. Platinum-catalyzed diyne cyclization/hydrosilylation tolerated a range of functional groups including esters, sulfones, acetals, silyl ethers, amides, and hindered ketones, Diynes that possessed propargylic substitution underwent facile cyclization/hydrosilylation to form silylated 1,2-dialkylidene cyclopentanes as mixtures of regioisomers. Diynes that possessed an electron-deficient internal alkyne underwent cyclization/hydrosilylation in moderate yield to form products resulting from silyl transfer to the less substituted alkyne. The silylated 1,2-dialkylidenecyclopentanes formed via diyne cyclization/hydrosilylation underwent a range of transformations including protodesilylation, Z/E isomerization, and [4 + 2] cycloaddition with dieneophiles. A 1:1 mixture of the platinum dimethyl diimine complex [PhN[double bond]C(Me)C(Me)[double bond]NPh]PtMe(2) (4a) and B(C(6)F(5))(3) catalyzed the cyclization/hydrosilylation of dimethyl dipropargylmalonate (1) and HSiEt(3) to form 1,1-dicarbomethoxy-3-methylene-4-(triethylsilylmethylene)cyclopentane (3) in 82% isolated yield with 26:1 Z:E selectivity. Platinum-catalyzed diyne cyclization/hydrosilylation tolerated a range of functional groups including esters, sulfones, acetals, silyl ethers, amides, and hindered ketones. Diynes that possessed propargylic substitution underwent facile cyclization/hydrosilylation to form silylated 1,2-dialkylidene cyclopentanes as mixtures of regioisomers. Diynes that possessed an electron-deficient internal alkyne underwent cyclization/hydrosilylation in moderate yield to form products resulting from silyl transfer to the less substituted alkyne. The silylated 1,2-dialkylidenecyclopentanes formed via diyne cyclization/hydrosilylation underwent a range of transformations including protodesilylation, Z/E isomerization, and [4 + 2] cycloaddition with dieneophiles. A 1:1 mixture of the platinum dimethyl diimine complex [PhNC(Me)C(Me)NPh]PtMe2 (4a) and B(C6F5)3 catalyzed the cyclization/hydrosilylation of dimethyl dipropargylmalonate (1) and HSiEt3 to form 1,1-dicarbomethoxy-3-methylene-4-(triethylsilylmethylene)cyclopentane (3) in 82% isolated yield with 26:1 Z:E selectivity. Platinum-catalyzed diyne cyclization/hydrosilylation tolerated a range of functional groups including esters, sulfones, acetals, silyl ethers, amides, and hindered ketones. Diynes that possessed propargylic substitution underwent facile cyclization/hydrosilylation to form silylated 1,2-dialkylidene cyclopentanes as mixtures of regioisomers. Diynes that possessed an electron-deficient internal alkyne underwent cyclization/hydrosilylation in moderate yield to form products resulting from silyl transfer to the less substituted alkyne. The silylated 1,2-dialkylidenecyclopentanes formed via diyne cyclization/hydrosilylation underwent a range of transformations including protodesilylation, Z/E isomerization, and [4 + 2] cycloaddition with dieneophiles. |
| Author | Wang, Xiang Madine, James W Widenhoefer, Ross A Keyerleber, Michele A Chakrapani, Harinath |
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| Keywords | ALPHA-OLEFINS BIS-DIENES 1,6-DIENES PYRIDINE-OXAZOLINE COMPLEXES PALLADIUM COMPLEX PHENANTHROLINE COMPLEX C-H ACTIVATION MEDIATED TETRAENE CARBOCYCLIZATIONS ENYNE COMPOUND CYCLIZATION Catalytic reaction Transition element complexes Sulfone Platinum Organic compounds Amides Organic silane Hydrosilylation Dienic compound Ketone Platinum I Complexes Acetal Ester Bidentate ligand Cycloaddition Cyclization Platinoid Complexes Transition metal Organic compounds Diynic compound Chemical synthesis Cyclopentane derivatives |
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| Snippet | A 1:1 mixture of the platinum dimethyl diimine complex [PhNC(Me)C(Me)NPh]PtMe2 (4a) and B(C6F5)3 catalyzed the cyclization/hydrosilylation of dimethyl... A 1:1 mixture of the platinum dimethyl diimine complex [PhNT=C(,Me)C(Me)=NPh]PtMe2 (4a) and B(C6F5)(3) catalyzed the cyclization/hydrosilylation of dimethyl... A 1:1 mixture of the platinum dimethyl diimine complex [PhN[double bond]C(Me)C(Me)[double bond]NPh]PtMe(2) (4a) and B(C(6)F(5))(3) catalyzed the... |
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| SubjectTerms | Alkynes - chemistry Catalysis Chemistry Chemistry, Organic Cyclization Drug Design Exact sciences and technology Hydrocarbons, Cyclic - chemical synthesis Magnetic Resonance Spectroscopy Models, Molecular Molecular Structure Nitrogen - chemistry Organic chemistry Organometalloidal and organometallic compounds Organoplatinum Compounds - chemistry Oxidation-Reduction Physical Sciences Preparations and properties Science & Technology Si derivatives Silanes - chemistry Stereoisomerism |
| Title | Cyclization/Hydrosilylation of Functionalized 1,6-Diynes Catalyzed by Cationic Platinum Complexes Containing Bidentate Nitrogen Ligands |
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