Visible-Light-Induced Organocatalytic Borylation of Aryl Chlorides
The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we ac...
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| Published in | Journal of the American Chemical Society Vol. 141; no. 23; pp. 9124 - 9128 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
12.06.2019
Amer Chemical Soc |
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| Online Access | Get full text |
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| Abstract | The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we achieved photoactivation of the in situ generated super electron donor and developed a visible-light-induced organocatalytic method for efficient borylation of unactivated aryl chlorides. |
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| AbstractList | The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we achieved photoactivation of the in situ generated super electron donor and developed a visible-light-induced organocatalytic method for efficient borylation of unactivated aryl chlorides. The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we achieved photo activation of the in situ generated super electron donor and developed a visible-light-induced organocatalytic method for efficient borylation of unactivated aryl chlorides. The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we achieved photoactivation of the in situ generated super electron donor and developed a visible-light-induced organocatalytic method for efficient borylation of unactivated aryl chlorides.The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we achieved photoactivation of the in situ generated super electron donor and developed a visible-light-induced organocatalytic method for efficient borylation of unactivated aryl chlorides. |
| Author | Jiao, Lei Zhang, Li |
| AuthorAffiliation | Center of Basic Molecular Science, Department of Chemistry |
| AuthorAffiliation_xml | – name: Center of Basic Molecular Science, Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Li surname: Zhang fullname: Zhang, Li – sequence: 2 givenname: Lei orcidid: 0000-0002-8465-1358 surname: Jiao fullname: Jiao, Lei email: Leijiao@mail.tsinghua.edu.cn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31140798$$D View this record in MEDLINE/PubMed |
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| Keywords | METAL-FREE BORYLATION HALIDES TRANSITION IODIDES ACTIVATION ELECTRON-TRANSFER FREE REDUCTIVE CLEAVAGE ALKOXY DIBORON REAGENTS CATALYZED BORYLATION BOND |
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| Snippet | The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to... |
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| SubjectTerms | boron compounds catalytic activity Chemistry Chemistry, Multidisciplinary organochlorine compounds Physical Sciences pyridines Science & Technology ultraviolet radiation |
| Title | Visible-Light-Induced Organocatalytic Borylation of Aryl Chlorides |
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