Site‐Selective Functionalization of Carboranes at the Electron‐Rich Boron Vertex: Photocatalytic B−C Coupling via a Carboranyl Cage Radical
Functionalization of carboranes in a vertex‐specific manner is a perennial challenge. Here, we report a photocatalytic B−C coupling for the selective functionalization of carboranes at the boron site which is most distal to carbon. This reaction was achieved by the photo‐induced decarboxylation of c...
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| Published in | Angewandte Chemie International Edition Vol. 61; no. 37; pp. e202205672 - n/a |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
Wiley Subscription Services, Inc
12.09.2022
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| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1433-7851 1521-3773 1521-3773 |
| DOI | 10.1002/anie.202205672 |
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| Abstract | Functionalization of carboranes in a vertex‐specific manner is a perennial challenge. Here, we report a photocatalytic B−C coupling for the selective functionalization of carboranes at the boron site which is most distal to carbon. This reaction was achieved by the photo‐induced decarboxylation of carborane carboxylic acids to generate boron vertex‐centered carboranyl radicals. Theoretical calculations also demonstrate that the reaction more easily occurs at the boron site bearing higher electron density owing to the lower energy barrier for a single‐electron transfer to generate a carboranyl radical. By using this strategy, a number of functionalized carboranes could be accessed through alkylation, alkenylation, and heteroarylation under mild conditions. Moreover, both a highly efficient blue emitter with a solid‐state luminous efficiency of 42 % and a drug candidate for boron neutron capture therapy (BNCT) containing targeting and fluorine units were obtained.
A new photocatalytic strategy for the site‐selective functionalization of carboranes was demonstrated by the photo‐induced decarboxylation of carborane carboxylic acids to generate boron‐vertex‐centered carboranyl radicals. This strategy enables facile construction of highly efficient blue emitters and drug candidates for boron neutron capture therapy (BNCT). |
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| AbstractList | Functionalization of carboranes in a vertex‐specific manner is a perennial challenge. Here, we report a photocatalytic B−C coupling for the selective functionalization of carboranes at the boron site which is most distal to carbon. This reaction was achieved by the photo‐induced decarboxylation of carborane carboxylic acids to generate boron vertex‐centered carboranyl radicals. Theoretical calculations also demonstrate that the reaction more easily occurs at the boron site bearing higher electron density owing to the lower energy barrier for a single‐electron transfer to generate a carboranyl radical. By using this strategy, a number of functionalized carboranes could be accessed through alkylation, alkenylation, and heteroarylation under mild conditions. Moreover, both a highly efficient blue emitter with a solid‐state luminous efficiency of 42 % and a drug candidate for boron neutron capture therapy (BNCT) containing targeting and fluorine units were obtained. Functionalization of carborane in a vertex-specific manner is a perennial challenge. Here, we report a photocatalytic B-C coupling for selective functionalization of carboranes at the boron site which is most distal to carbon. This reaction protocol was achieved by photo-induced decarboxylation of carborane carboxylic acids to generate boron vertex-centered carboranyl radicals. Theoretical calculations also demonstrate that the reaction more easily occurs at the boron site bearing higher electron density owing to the lower energy barrier for a single electron transfer to generate a carboranyl radical. By using this strategy, a number of functionalized carboranes through alkylation, alkenylation, and heteroarylation could be accessed under mild conditions. Moreover, both a highly efficient blue emitter with the solid-state luminous efficiency of 42% and a Boron Neutron Capture Therapy (BNCT) drug candidate containing targeting and fluorine units were obtained. Functionalization of carboranes in a vertex‐specific manner is a perennial challenge. Here, we report a photocatalytic B−C coupling for the selective functionalization of carboranes at the boron site which is most distal to carbon. This reaction was achieved by the photo‐induced decarboxylation of carborane carboxylic acids to generate boron vertex‐centered carboranyl radicals. Theoretical calculations also demonstrate that the reaction more easily occurs at the boron site bearing higher electron density owing to the lower energy barrier for a single‐electron transfer to generate a carboranyl radical. By using this strategy, a number of functionalized carboranes could be accessed through alkylation, alkenylation, and heteroarylation under mild conditions. Moreover, both a highly efficient blue emitter with a solid‐state luminous efficiency of 42 % and a drug candidate for boron neutron capture therapy (BNCT) containing targeting and fluorine units were obtained. A new photocatalytic strategy for the site‐selective functionalization of carboranes was demonstrated by the photo‐induced decarboxylation of carborane carboxylic acids to generate boron‐vertex‐centered carboranyl radicals. This strategy enables facile construction of highly efficient blue emitters and drug candidates for boron neutron capture therapy (BNCT). Functionalization of carboranes in a vertex-specific manner is a perennial challenge. Here, we report a photocatalytic B-C coupling for the selective functionalization of carboranes at the boron site which is most distal to carbon. This reaction was achieved by the photo-induced decarboxylation of carborane carboxylic acids to generate boron vertex-centered carboranyl radicals. Theoretical calculations also demonstrate that the reaction more easily occurs at the boron site bearing higher electron density owing to the lower energy barrier for a single-electron transfer to generate a carboranyl radical. By using this strategy, a number of functionalized carboranes could be accessed through alkylation, alkenylation, and heteroarylation under mild conditions. Moreover, both a highly efficient blue emitter with a solid-state luminous efficiency of 42 % and a drug candidate for boron neutron capture therapy (BNCT) containing targeting and fluorine units were obtained.Functionalization of carboranes in a vertex-specific manner is a perennial challenge. Here, we report a photocatalytic B-C coupling for the selective functionalization of carboranes at the boron site which is most distal to carbon. This reaction was achieved by the photo-induced decarboxylation of carborane carboxylic acids to generate boron vertex-centered carboranyl radicals. Theoretical calculations also demonstrate that the reaction more easily occurs at the boron site bearing higher electron density owing to the lower energy barrier for a single-electron transfer to generate a carboranyl radical. By using this strategy, a number of functionalized carboranes could be accessed through alkylation, alkenylation, and heteroarylation under mild conditions. Moreover, both a highly efficient blue emitter with a solid-state luminous efficiency of 42 % and a drug candidate for boron neutron capture therapy (BNCT) containing targeting and fluorine units were obtained. |
| Author | Tu, Deshuang Tian, Songlin Sun, Fangxiang Chen, Meng Xu, Jingkai Lu, Changsheng Zhao, Deshi Yan, Hong |
| Author_xml | – sequence: 1 givenname: Meng surname: Chen fullname: Chen, Meng organization: Nanjing University – sequence: 2 givenname: Jingkai orcidid: 0000-0002-7545-3608 surname: Xu fullname: Xu, Jingkai organization: Nanjing University – sequence: 3 givenname: Deshi surname: Zhao fullname: Zhao, Deshi organization: Nanjing University – sequence: 4 givenname: Fangxiang surname: Sun fullname: Sun, Fangxiang organization: Nanjing University – sequence: 5 givenname: Songlin surname: Tian fullname: Tian, Songlin organization: Nanjing University – sequence: 6 givenname: Deshuang surname: Tu fullname: Tu, Deshuang email: tudeshuang@126.com organization: Nanjing University – sequence: 7 givenname: Changsheng surname: Lu fullname: Lu, Changsheng email: luchsh@nju.edu.cn organization: Nanjing University – sequence: 8 givenname: Hong orcidid: 0000-0003-3993-0013 surname: Yan fullname: Yan, Hong email: hyan1965@nju.edu.cn organization: Nanjing University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/35670361$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1021_acs_accounts_2c00752 crossref_primary_10_1039_D4SC02214A crossref_primary_10_1002_anie_202305088 crossref_primary_10_1002_ange_202305088 crossref_primary_10_1002_cjoc_202200622 crossref_primary_10_1021_acs_orglett_2c02648 crossref_primary_10_1039_D2CY01703B crossref_primary_10_1039_D4SC08085H crossref_primary_10_1021_jacs_4c00550 crossref_primary_10_1002_ajoc_202200630 crossref_primary_10_1021_jacs_3c00866 crossref_primary_10_1021_jacs_4c16062 crossref_primary_10_1039_D4QI02011A crossref_primary_10_1039_D4CP03615H crossref_primary_10_1039_D5SC00234F crossref_primary_10_1021_acs_orglett_2c02590 crossref_primary_10_1039_D4QO01428F crossref_primary_10_1002_adsc_202201183 crossref_primary_10_1021_acs_orglett_3c01989 crossref_primary_10_3390_molecules29163916 |
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| Keywords | boron chemistry B−C Coupling Carboranes Boron-Cluster Materials Carboranyl Radicals |
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| Snippet | Functionalization of carboranes in a vertex‐specific manner is a perennial challenge. Here, we report a photocatalytic B−C coupling for the selective... Functionalization of carborane in a vertex-specific manner is a perennial challenge. Here, we report a photocatalytic B-C coupling for selective... Functionalization of carboranes in a vertex-specific manner is a perennial challenge. Here, we report a photocatalytic B-C coupling for the selective... |
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| SubjectTerms | Alkylation Boron Boron Chemistry Boron-Cluster Materials B−C Coupling Carborane Carboranes Carboranyl Radicals Carboxylic acids Coupling Decarboxylation Drug development Electron density Electron transfer Emitters Fluorine Luminous efficacy Nuclear capture |
| Title | Site‐Selective Functionalization of Carboranes at the Electron‐Rich Boron Vertex: Photocatalytic B−C Coupling via a Carboranyl Cage Radical |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202205672 https://www.ncbi.nlm.nih.gov/pubmed/35670361 https://www.proquest.com/docview/2709714086 https://www.proquest.com/docview/2674005790 |
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