Rhodium-catalyzed triazole-directed C-H bond functionalization of arenes with diazo compounds
Heterocyclic compounds bearing 1,2,3-triazole scaffolds have found wide application both in medicinal chemistry and materials science. In this paper, rhodium(iii)-catalyzed triazole-directed alkylation reactions of arenes using diazo compounds as the alkylating agents are described. A number of poly...
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| Published in | Organic & biomolecular chemistry Vol. 16; no. 43; pp. 8191 - 8195 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
07.11.2018
Royal Society of Chemistry |
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| Abstract | Heterocyclic compounds bearing 1,2,3-triazole scaffolds have found wide application both in medicinal chemistry and materials science. In this paper, rhodium(iii)-catalyzed triazole-directed alkylation reactions of arenes using diazo compounds as the alkylating agents are described. A number of polysubstituted arenes were provided from easily available materials in good yields under mild conditions. The reactions proceed via triazole-directed ortho C-H bond activation and subsequent carbene insertion originating from diazo compounds. |
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| AbstractList | Heterocyclic compounds bearing 1,2,3-triazole scaffolds have found wide application both in medicinal chemistry and materials science. In this paper, rhodium(iii)-catalyzed triazole-directed alkylation reactions of arenes using diazo compounds as the alkylating agents are described. A number of polysubstituted arenes were provided from easily available materials in good yields under mild conditions. The reactions proceed via triazole-directed ortho C-H bond activation and subsequent carbene insertion originating from diazo compounds. Heterocyclic compounds bearing 1,2,3-triazole scaffolds have found wide application both in medicinal chemistry and materials science. In this paper, rhodium( iii )-catalyzed triazole-directed alkylation reactions of arenes using diazo compounds as the alkylating agents are described. A number of polysubstituted arenes were provided from easily available materials in good yields under mild conditions. The reactions proceed via triazole-directed ortho C–H bond activation and subsequent carbene insertion originating from diazo compounds. |
| Author | Yi, Xiaofei Chen, Wanzhi Cui, Yanli Wang, Huanhong |
| Author_xml | – sequence: 1 givenname: Huanhong surname: Wang fullname: Wang, Huanhong organization: Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China – sequence: 2 givenname: Xiaofei surname: Yi fullname: Yi, Xiaofei organization: Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China – sequence: 3 givenname: Yanli surname: Cui fullname: Cui, Yanli email: cuiyl@zju.edu.cn organization: Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China – sequence: 4 givenname: Wanzhi orcidid: 0000-0002-7076-1521 surname: Chen fullname: Chen, Wanzhi email: chenwzz@zju.edu.cn organization: Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30357225$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1021_acs_orglett_0c02893 crossref_primary_10_1039_D1OB00195G crossref_primary_10_1002_adsc_201901193 crossref_primary_10_1021_acs_orglett_0c01517 crossref_primary_10_1039_C9DT00421A crossref_primary_10_1002_asia_201901620 crossref_primary_10_1016_j_ccr_2019_213051 crossref_primary_10_1002_asia_202001219 crossref_primary_10_6023_A22040147 crossref_primary_10_1002_tcr_202100193 crossref_primary_10_1039_D1CS00895A crossref_primary_10_1016_j_tet_2020_130985 crossref_primary_10_1021_acs_organomet_9b00440 crossref_primary_10_1002_cctc_202002016 crossref_primary_10_1039_D0QO01571G crossref_primary_10_1021_acs_joc_9b00058 |
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| Keywords | ACTIVATION AZIDES OLEFINATION ANNULATION 1,2,3-TRIAZOLES 1,3-DIPOLAR CYCLOADDITION REGIOSELECTIVE SYNTHESIS NITROOLEFINS ALKYNES CYCLIZATION |
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| Snippet | Heterocyclic compounds bearing 1,2,3-triazole scaffolds have found wide application both in medicinal chemistry and materials science. In this paper,... Heterocyclic compounds bearing 1,2,3-triazole scaffolds have found wide application both in medicinal chemistry and materials science. In this paper, rhodium(... |
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| SubjectTerms | Alkylating agents Alkylation Aromatic compounds Catalysis Chemical reactions Chemistry Chemistry, Organic Crystallography Data processing Heterocyclic compounds Hydrogen bonds Materials science Organic chemistry Physical Sciences Rhodium Science & Technology |
| Title | Rhodium-catalyzed triazole-directed C-H bond functionalization of arenes with diazo compounds |
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