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Aerobic Copper-Catalyzed Salicylaldehydic C formyl -H Arylations with Arylboronic Acids
We report a challenging copper-catalyzed C -H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the C -H bond compared to the...
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| Published in: | Chemistry : a European journal 2021-02, Vol.27 (10), p.3278-3283 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c192t-36e498292d72cf511a2025e7eec2917cf81bfe802d51e3416c3cf3ec515396b33 |
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| cites | cdi_FETCH-LOGICAL-c192t-36e498292d72cf511a2025e7eec2917cf81bfe802d51e3416c3cf3ec515396b33 |
| container_end_page | 3283 |
| container_issue | 10 |
| container_start_page | 3278 |
| container_title | Chemistry : a European journal |
| container_volume | 27 |
| creator | Xiao, Lin Lang, Tao-Tao Jiang, Ying Zang, Zhong-Lin Zhou, Cheng-He Cai, Gui-Xin |
| description | We report a challenging copper-catalyzed C
-H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the C
-H bond compared to the phenolic O-H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a Cu
/Cu
/Cu
catalytic cycle. |
| doi_str_mv | 10.1002/chem.202004810 |
| format | article |
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-H bond compared to the phenolic O-H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a Cu
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/Cu
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-H bond compared to the phenolic O-H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a Cu
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-H bond compared to the phenolic O-H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a Cu
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/Cu
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| ispartof | Chemistry : a European journal, 2021-02, Vol.27 (10), p.3278-3283 |
| issn | 0947-6539 1521-3765 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_chem_202004810 |
| source | Wiley |
| title | Aerobic Copper-Catalyzed Salicylaldehydic C formyl -H Arylations with Arylboronic Acids |
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