Visible-Light Copper Nanocluster Catalysis for the C–N Coupling of Aryl Chlorides at Room Temperature
Activation of aryl chlorides in cross-coupling reactions is a long-standing challenge in organic synthesis that is of great interest to industry. Ultrasmall (<3 nm), atomically precise nanoclusters (NCs) are considered one of the most promising catalysts due to their high surface area and unsatur...
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| Published in | Journal of the American Chemical Society Vol. 144; no. 27; pp. 12052 - 12061 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
American Chemical Society
13.07.2022
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| Subjects | |
| Online Access | Get full text |
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| Abstract | Activation of aryl chlorides in cross-coupling reactions is a long-standing challenge in organic synthesis that is of great interest to industry. Ultrasmall (<3 nm), atomically precise nanoclusters (NCs) are considered one of the most promising catalysts due to their high surface area and unsaturated active sites. Herein, we introduce a copper nanocluster-based catalyst, [Cu61(StBu)26S6Cl6H14] (Cu61NC) that enables C–N bond-forming reactions of aryl chlorides under visible-light irradiation at room temperature. A range of N-heterocyclic nucleophiles and electronically and sterically diverse aryl/hetero chlorides react in this new Cu61NC-catalyzed process to afford the C–N coupling products in good yields. Mechanistic studies indicate that a single-electron-transfer (SET) process between the photoexcited Cu61NC complex and aryl halide enables the C–N-arylation reaction. |
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| AbstractList | Activation of aryl chlorides in cross-coupling reactions is a long-standing challenge in organic synthesis that is of great interest to industry. Ultrasmall (<3 nm), atomically precise nanoclusters (NCs) are considered one of the most promising catalysts due to their high surface area and unsaturated active sites. Herein, we introduce a copper nanocluster-based catalyst, [Cu61(StBu)26S6Cl6H14] (Cu61NC) that enables C–N bond-forming reactions of aryl chlorides under visible-light irradiation at room temperature. A range of N-heterocyclic nucleophiles and electronically and sterically diverse aryl/hetero chlorides react in this new Cu61NC-catalyzed process to afford the C–N coupling products in good yields. Mechanistic studies indicate that a single-electron-transfer (SET) process between the photoexcited Cu61NC complex and aryl halide enables the C–N-arylation reaction. Activation of aryl chlorides in cross-coupling reactions is a long-standing challenge in organic synthesis that is of great interest to industry. Ultrasmall (<3 nm), atomically precise nanoclusters (NCs) are considered one of the most promising catalysts due to their high surface area and unsaturated active sites. Herein, we introduce a copper nanocluster-based catalyst, [Cu₆₁(SᵗBu)₂₆S₆Cl₆H₁₄] (Cu₆₁NC) that enables C–N bond-forming reactions of aryl chlorides under visible-light irradiation at room temperature. A range of N-heterocyclic nucleophiles and electronically and sterically diverse aryl/hetero chlorides react in this new Cu₆₁NC-catalyzed process to afford the C–N coupling products in good yields. Mechanistic studies indicate that a single-electron-transfer (SET) process between the photoexcited Cu₆₁NC complex and aryl halide enables the C–N-arylation reaction. Activation of aryl chlorides in cross-coupling reactions is a long-standing challenge in organic synthesis that is of great interest to industry. Ultrasmall (<3 nm), atomically precise nanoclusters (NCs) are considered one of the most promising catalysts due to their high surface area and unsaturated active sites. Herein, we introduce a copper nanocluster-based catalyst, [Cu61(StBu)26S6Cl6H14] (Cu61NC) that enables C-N bond-forming reactions of aryl chlorides under visible-light irradiation at room temperature. A range of N-heterocyclic nucleophiles and electronically and sterically diverse aryl/hetero chlorides react in this new Cu61NC-catalyzed process to afford the C-N coupling products in good yields. Mechanistic studies indicate that a single-electron-transfer (SET) process between the photoexcited Cu61NC complex and aryl halide enables the C-N-arylation reaction.Activation of aryl chlorides in cross-coupling reactions is a long-standing challenge in organic synthesis that is of great interest to industry. Ultrasmall (<3 nm), atomically precise nanoclusters (NCs) are considered one of the most promising catalysts due to their high surface area and unsaturated active sites. Herein, we introduce a copper nanocluster-based catalyst, [Cu61(StBu)26S6Cl6H14] (Cu61NC) that enables C-N bond-forming reactions of aryl chlorides under visible-light irradiation at room temperature. A range of N-heterocyclic nucleophiles and electronically and sterically diverse aryl/hetero chlorides react in this new Cu61NC-catalyzed process to afford the C-N coupling products in good yields. Mechanistic studies indicate that a single-electron-transfer (SET) process between the photoexcited Cu61NC complex and aryl halide enables the C-N-arylation reaction. |
| Author | Mohammed, Omar F. Sagadevan, Arunachalam Maity, Partha Rueping, Magnus Ghosh, Atanu Bakr, Osman M. |
| AuthorAffiliation | KAUST Catalysis Center (KCC) |
| AuthorAffiliation_xml | – name: KAUST Catalysis Center (KCC) |
| Author_xml | – sequence: 1 givenname: Arunachalam surname: Sagadevan fullname: Sagadevan, Arunachalam – sequence: 2 givenname: Atanu orcidid: 0000-0002-4938-8793 surname: Ghosh fullname: Ghosh, Atanu – sequence: 3 givenname: Partha orcidid: 0000-0002-0293-7118 surname: Maity fullname: Maity, Partha – sequence: 4 givenname: Omar F. orcidid: 0000-0001-8500-1130 surname: Mohammed fullname: Mohammed, Omar F. – sequence: 5 givenname: Osman M. orcidid: 0000-0002-3428-1002 surname: Bakr fullname: Bakr, Osman M. email: osman.bakr@kaust.edu.sa – sequence: 6 givenname: Magnus orcidid: 0000-0003-4580-5227 surname: Rueping fullname: Rueping, Magnus email: magnus.rueping@Kaust.edu.sa |
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| Title | Visible-Light Copper Nanocluster Catalysis for the C–N Coupling of Aryl Chlorides at Room Temperature |
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