Competing Dehalogenation versus Borylation of Aryl Iodides and Bromides under Transition-Metal-Free Basic Conditions
In this work, selectivity-controllable base-promoted transition-metal-free borylation and dehalogenation of aryl halides are described. Under the conditions of borylation, the dehalogenation which emerges as a competitive side reaction has been well-controlled by carefully controlling the borylation...
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| Published in | Journal of organic chemistry Vol. 84; no. 17; pp. 10805 - 10813 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
06.09.2019
Amer Chemical Soc |
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| Abstract | In this work, selectivity-controllable base-promoted transition-metal-free borylation and dehalogenation of aryl halides are described. Under the conditions of borylation, the dehalogenation which emerges as a competitive side reaction has been well-controlled by carefully controlling the borylation conditions. On the other hand, the dehalogenation using benzaldehyde as a hydrogen source has also been accomplished. The applications of direct radical borylation and dehalogenation of aryl halides demonstrate their synthetic practicability in pharmaceutical-oriented organic synthesis. Based on the experimental evidences, the t BuOK/1,10-Phen-triggered radical nature of both competitive reactions has been revealed. |
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| AbstractList | In this work, selectivity-controllable base-promoted transition-metal-free borylation and dehalogenation of aryl halides are described. Under the conditions of borylation, the dehalogenation which emerges as a competitive side reaction has been well-controlled by carefully controlling the borylation conditions. On the other hand, the dehalogenation using benzaldehyde as a hydrogen source has also been accomplished. The applications of direct radical borylation and dehalogenation of aryl halides demonstrate their synthetic practicability in pharmaceutical-oriented organic synthesis. Based on the experimental evidences, the t BuOK/1,10-Phen-triggered radical nature of both competitive reactions has been revealed. In this work, a selectivity-controllable base-promoted transition metal-free borylation and dehalogenation of aryl halides are described. Under the conditions of borylation, the dehalogenation which emerges as a competitive side-reaction has been well-controlled by carefully controlling the borylation conditions. On the other hand, the dehalogenation using benzaldehyde as hydrogen source has also been accomplished. The applications of direct radical borylation and dehalogenation of aryl halides demonstrate their synthetic practicability in pharmaceutical-oriented organic synthesis. Based on the experimental evidences, the tBuOK/1,10-Phen triggered radical nature of both competitive reactions has been revealed. In this work, selectivity-controllable base-promoted transition-metal-free borylation and dehalogenation of aryl halides are described. Under the conditions of borylation, the dehalogenation which emerges as a competitive side reaction has been well-controlled by carefully controlling the borylation conditions. On the other hand, the dehalogenation using benzaldehyde as a hydrogen source has also been accomplished. The applications of direct radical borylation and dehalogenation of aryl halides demonstrate their synthetic practicability in pharmaceutical-oriented organic synthesis. Based on the experimental evidences, the (BuOK)-Bu-t/1,10-Phen-triggered radical nature of both competitive reactions has been revealed. |
| Author | Shan, Xiang-Huan Fu, Jia-Le Kang, Yan-Biao Zheng, Hong-Xing Niu, Yi-Jie Tie, Lin Sui, Guo-Hui Qu, Jian-Ping |
| AuthorAffiliation | Department of Chemistry Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials School of Chemistry and Chemical Engineering Liaocheng University |
| AuthorAffiliation_xml | – name: Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials – name: Liaocheng University – name: School of Chemistry and Chemical Engineering – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Yi-Jie surname: Niu fullname: Niu, Yi-Jie organization: Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials – sequence: 2 givenname: Guo-Hui surname: Sui fullname: Sui, Guo-Hui organization: Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials – sequence: 3 givenname: Hong-Xing surname: Zheng fullname: Zheng, Hong-Xing organization: Liaocheng University – sequence: 4 givenname: Xiang-Huan surname: Shan fullname: Shan, Xiang-Huan organization: Department of Chemistry – sequence: 5 givenname: Lin surname: Tie fullname: Tie, Lin organization: Department of Chemistry – sequence: 6 givenname: Jia-Le surname: Fu fullname: Fu, Jia-Le organization: Department of Chemistry – sequence: 7 givenname: Jian-Ping orcidid: 0000-0002-5002-5594 surname: Qu fullname: Qu, Jian-Ping email: ias_jpqu@njtech.edu.cn organization: Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials – sequence: 8 givenname: Yan-Biao orcidid: 0000-0002-7537-4627 surname: Kang fullname: Kang, Yan-Biao email: ybkang@ustc.edu.cn organization: Department of Chemistry |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31418570$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1002_ejoc_202201379 crossref_primary_10_1039_D3NJ03228K crossref_primary_10_1007_s11237_023_09775_4 crossref_primary_10_1021_acs_orglett_0c01615 crossref_primary_10_1039_D0CC01172J crossref_primary_10_3390_molecules26216374 crossref_primary_10_1021_acs_orglett_0c00827 crossref_primary_10_1002_slct_202203856 crossref_primary_10_1002_ajoc_202100645 crossref_primary_10_1142_S1088424623500815 crossref_primary_10_1002_chem_202200556 crossref_primary_10_1039_D4RA00487F crossref_primary_10_1002_ange_202100569 crossref_primary_10_1002_anie_202100569 |
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| Keywords | PALLADIUM CROSS-COUPLING REACTIONS ELECTRON ACTIVATION REDUCTION SECONDARY ORGANIC HALIDES COPPER-CATALYZED BORYLATION ALKOXY DIBORON REAGENTS ALKYL-HALIDES |
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| Snippet | In this work, selectivity-controllable base-promoted transition-metal-free borylation and dehalogenation of aryl halides are described. Under the conditions of... In this work, a selectivity-controllable base-promoted transition metal-free borylation and dehalogenation of aryl halides are described. Under the conditions... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Competing Dehalogenation versus Borylation of Aryl Iodides and Bromides under Transition-Metal-Free Basic Conditions |
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