Sie befinden Sich nicht im Netzwerk der Universität Paderborn. Der Zugriff auf elektronische Ressourcen ist gegebenenfalls nur via VPN oder Shibboleth (DFN-AAI) möglich. mehr Informationen...
Introducing Trifluoromethoxyarenes as Halide Surrogates in Mechanochemical Realizations of Ni‐catalyzed Cross‐coupling Reactions
Ist Teil von
Asian journal of organic chemistry, 2023-06, Vol.12 (6), p.n/a
Ort / Verlag
Weinheim: Wiley Subscription Services, Inc
Erscheinungsjahr
2023
Quelle
Wiley InterScience Journals
Beschreibungen/Notizen
Since the introduction of the TM‐catalyzed cross‐couplings their scope of starting materials has been growing systematically, allowing for more flexible design of synthetic routes with the coupling as a key step, particularly late‐stage modifications. Herein we present the use of trifluoromethoxyarenes as halide surrogates in Ni‐catalyzed couplings with arylboronic acids, potassium aryl trifluoroborates and aryl trialkoxysilanes, under mechanochemical conditions. In total, 22 biphenyl structures were obtained in good yields. Successful gram scale experiments confirm the usefulness of our protocol. The developed transformations’ mechanism was discussed in relation to the experimental and literature data and DFT calculations. The unusual reactivity of potassium benzoyltrifluoroborates was uncovered. 6 examples of resulting benzophenones were obtained in very good yields and the protocol was extended to gram scale. The described methods present a powerful tool when combined with the recent advances in organofluorine chemistry.
Trifluoromethoxyarenes were identified as halide surrogates in Ni‐catalyzed couplings with arylboronic acids, potassium aryl trifluoroborates and aryl trialkoxysilanes, under mechanochemical conditions. Unusual reactivity of potassium benzoyltrifluoroborates was uncovered. Resulting benzophenones were obtained in very good yields. The described methods present a powerful tool when combined with the recent advances in organofluorine chemistry.