Copper/P(tBu)3‐Mediated Regiospecific Synthesis of Fused Furans and Naphthofurans
A novel [3+2] cycloaddition between a variety of cyclic ketones and diverse olefins or alkynes can be effectively promoted by copper in combination with the tri‐tert‐butylphosphine [P(tBu)3] ligand. This protocol exhibits excellent selectivity and provides an exemplary set of fused heterocycles in g...
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| Published in | Angewandte Chemie International Edition Vol. 56; no. 4; pp. 1111 - 1115 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
Wiley Subscription Services, Inc
19.01.2017
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| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | A novel [3+2] cycloaddition between a variety of cyclic ketones and diverse olefins or alkynes can be effectively promoted by copper in combination with the tri‐tert‐butylphosphine [P(tBu)3] ligand. This protocol exhibits excellent selectivity and provides an exemplary set of fused heterocycles in good to excellent yields. Present strategy also represents an extremely simple and atom‐economic way to construct substituted fused furans and naphthofurans from readily available starting materials under mild reaction conditions. The utility of the method is further demonstrated by the synthesis of chiral furans from (R)‐(−)‐carvone and (S)‐(+)‐carvone. A plausible mechanism involving the oxidative radical cyclization has been suggested based on experimental observations.
Fusion chemistry: A novel [3+2] cycloaddition between a variety of cyclic ketones and olefins is effectively promoted by Cu/P(tBu)3. The protocol provides fused heterocycles in good to excellent yields, and is an atom‐economic way to construct fused furans and naphthofurans from readily available starting materials under mild reaction conditions. A mechanism involving an oxidative radical cyclization is suggested. |
|---|---|
| AbstractList | Abstract
A novel [3+2] cycloaddition between a variety of cyclic ketones and diverse olefins or alkynes can be effectively promoted by copper in combination with the tri‐
tert
‐butylphosphine [P(
t
Bu)
3
] ligand. This protocol exhibits excellent selectivity and provides an exemplary set of fused heterocycles in good to excellent yields. Present strategy also represents an extremely simple and atom‐economic way to construct substituted fused furans and naphthofurans from readily available starting materials under mild reaction conditions. The utility of the method is further demonstrated by the synthesis of chiral furans from (
R
)‐(−)‐carvone and (
S
)‐(+)‐carvone. A plausible mechanism involving the oxidative radical cyclization has been suggested based on experimental observations. A novel [3+2] cycloaddition between a variety of cyclic ketones and diverse olefins or alkynes can be effectively promoted by copper in combination with the tri-tert-butylphosphine [P(tBu) ] ligand. This protocol exhibits excellent selectivity and provides an exemplary set of fused heterocycles in good to excellent yields. Present strategy also represents an extremely simple and atom-economic way to construct substituted fused furans and naphthofurans from readily available starting materials under mild reaction conditions. The utility of the method is further demonstrated by the synthesis of chiral furans from (R)-(-)-carvone and (S)-(+)-carvone. A plausible mechanism involving the oxidative radical cyclization has been suggested based on experimental observations. A novel [3+2] cycloaddition between a variety of cyclic ketones and diverse olefins or alkynes can be effectively promoted by copper in combination with the tri‐tert‐butylphosphine [P(tBu)3] ligand. This protocol exhibits excellent selectivity and provides an exemplary set of fused heterocycles in good to excellent yields. Present strategy also represents an extremely simple and atom‐economic way to construct substituted fused furans and naphthofurans from readily available starting materials under mild reaction conditions. The utility of the method is further demonstrated by the synthesis of chiral furans from (R)‐(−)‐carvone and (S)‐(+)‐carvone. A plausible mechanism involving the oxidative radical cyclization has been suggested based on experimental observations. A novel [3+2] cycloaddition between a variety of cyclic ketones and diverse olefins or alkynes can be effectively promoted by copper in combination with the tri-tert-butylphosphine [P(tBu)3 ] ligand. This protocol exhibits excellent selectivity and provides an exemplary set of fused heterocycles in good to excellent yields. Present strategy also represents an extremely simple and atom-economic way to construct substituted fused furans and naphthofurans from readily available starting materials under mild reaction conditions. The utility of the method is further demonstrated by the synthesis of chiral furans from (R)-(-)-carvone and (S)-(+)-carvone. A plausible mechanism involving the oxidative radical cyclization has been suggested based on experimental observations. A novel [3+2] cycloaddition between a variety of cyclic ketones and diverse olefins or alkynes can be effectively promoted by copper in combination with the tri‐tert‐butylphosphine [P(tBu)3] ligand. This protocol exhibits excellent selectivity and provides an exemplary set of fused heterocycles in good to excellent yields. Present strategy also represents an extremely simple and atom‐economic way to construct substituted fused furans and naphthofurans from readily available starting materials under mild reaction conditions. The utility of the method is further demonstrated by the synthesis of chiral furans from (R)‐(−)‐carvone and (S)‐(+)‐carvone. A plausible mechanism involving the oxidative radical cyclization has been suggested based on experimental observations. Fusion chemistry: A novel [3+2] cycloaddition between a variety of cyclic ketones and olefins is effectively promoted by Cu/P(tBu)3. The protocol provides fused heterocycles in good to excellent yields, and is an atom‐economic way to construct fused furans and naphthofurans from readily available starting materials under mild reaction conditions. A mechanism involving an oxidative radical cyclization is suggested. |
| Author | Naveen, Togati Maiti, Debabrata Deb, Arghya |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27996192$$D View this record in MEDLINE/PubMed |
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| Copyright | 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Keywords | copper P ligands cycloaddition heterocycles olefins |
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| Snippet | A novel [3+2] cycloaddition between a variety of cyclic ketones and diverse olefins or alkynes can be effectively promoted by copper in combination with the... Abstract A novel [3+2] cycloaddition between a variety of cyclic ketones and diverse olefins or alkynes can be effectively promoted by copper in combination... |
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| SubjectTerms | Alkenes Alkynes Atom economy Carvone Copper Cycloaddition Furans heterocycles Ketones olefins Pesticides P ligands Synthesis |
| Title | Copper/P(tBu)3‐Mediated Regiospecific Synthesis of Fused Furans and Naphthofurans |
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