https://scholars.lib.ntu.edu.tw/handle/123456789/632758
Title: | Palladium-catalyzed vinylation of cyclohexenes using a directing-group strategy | Authors: | Yen, CT Liu, YH SHIUH-TZUNG LIU |
Keywords: | Aza-Heck reaction; cyclohexene; E; palladium; vinylation; AZA-HECK CYCLIZATIONS | Issue Date: | 2023 | Publisher: | WILEY-V C H VERLAG GMBH | Journal Volume: | 70 | Journal Issue: | 5 | Start page/Pages: | 1136 | Source: | JOURNAL OF THE CHINESE CHEMICAL SOCIETY | Abstract: | Palladium-promoted vinylation of cyclohexenes via employment of a directing-group strategy to yield the coupled vinyl cyclohexenes with excellent regio- and stereoselectivity was studied. Typically, reaction of 2-(cyclohex-2-en-1-yl)-N-tosylacetamide (1a) with (Z)-styryl bromides (2) gave cis-2-[(E)-styryl]cyclopent-3-en-1-yl-N-tosylacetamides in good to excellent yields. It is noticed that (Z)-styryl moiety was inverted into (E)-form in products. Unfortunately, (E)-styryl bromide substrates were not suitable for this reaction under the condition investigated. Further studies on norbornene system, we found that palladium-catalyzed reaction of endo-N-tosylbicyclo[2.2.1]hept-5-ene-2-carboxamide (6) with styryl bromides gave the Aza-Heck type products. |
URI: | https://scholars.lib.ntu.edu.tw/handle/123456789/632758 | ISSN: | 0009-4536 | DOI: | 10.1002/jccs.202200529 |
Appears in Collections: | 化學系 |
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