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Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N-Heterocycles
Grace L. Trammel ; Prashansa B. Kannangara ; Dmytro Vasko , et al. Angew. Chem. Int. Ed.,2022,61,e20221211. DOI: 10.1002/anie.202212117 PubMed ID: 36250954
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Abstract: Two catalytic systems have been developed for the arylboration of endocyclic enecarbamates to deliver synthetically versatile borylated saturated Nheterocycles in good regio- and diastereoselectivities. A Cu/Pd dual catalytic reaction enables the synthesis of borylated, α-arylated azetidines, while a Ni-catalysed arylboration reaction efficiently functionalizes 5-, 6-, and 7-membered enecarbamates. In the case of the Cu/Pdsystem, a remarkable additive effect was identified that allowed for broader scope. The products are synthetically useful, as demonstrated by manipulations of the boronic ester to access biologically active compounds.
Keywords: Alkene ; Arylation ; Boron ; Cross Coupling ; Heterocycle
Purchased from AmBeed: 100367-39-3 ; 66899-02-3 ; 3964-04-3 ; 108963-96-8
CAS No. : | 3964-04-3 | MDL No. : | MFCD07644514 |
Formula : | C9H6BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SUXIPCHEUMEUSV-UHFFFAOYSA-N |
M.W : | 208.05 | Pubchem ID : | 11735918 |
Synonyms : |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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