Multigram Synthesis of Heterabicyclo[n.1.0]alkan‐1‐yl Trifluoroborates

An approach to the synthesis of oxa‐ and azabicyclo[n.1.0]alkan‐1‐yl trifluoroborates on a multigram scale was developed. Two synthetic strategies were evaluated: the first based on the lithiation–borylation of the corresponding 2‐bromoallyl derivatives, and the other relying on regioselective hydro...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-12, Vol.2021 (47), p.6551-6560
Main Authors: Kleban, Ihor, Krokhmaliuk, Yevhen, Reut, Sofiia, Shuvakin, Serhii, Pendyukh, Vyacheslav V., Khyzhan, Oleksandr I., Yarmoliuk, Dmytro S., Tymtsunik, Andriy V., Rassukana, Yuliya V., Grygorenko, Oleksandr O.
Format: Article
Language:English
Subjects:
Bicyclic compounds
Cyclopropanes
Heteroaliphatic compounds
Organoboron compounds
Suzuki–Miyaura reaction
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Summary:An approach to the synthesis of oxa‐ and azabicyclo[n.1.0]alkan‐1‐yl trifluoroborates on a multigram scale was developed. Two synthetic strategies were evaluated: the first based on the lithiation–borylation of the corresponding 2‐bromoallyl derivatives, and the other relying on regioselective hydroboration of the appropriate hetera‐substituted enynes. The second method appeared to be more efficient in terms of scalability and substrate scope. Further steps included ring closing‐metathesis, mild palladium‐catalyzed cyclopropanation with diazomethane, and reaction with KHF2 and furnished the title compounds in up to 50 g scale in a single run (10–41 % overall yield, 4–5 steps). Multigram synthesis of oxa‐ and azabicyclo[n.1.0]alkan‐1‐yl trifluoroborates relying on efficient 4–5‐step reaction sequences is described. The title compounds was obtained in up to 50 g scale in a single run (10–41 % overall yield).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000977