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Abstract The development of pyridylidene‐Cu‐complexes and their application in Cu/Pd‐catalyzed heteroarylboration of alkenylheteroarenes is reported. The significance of 1,1′‐heteroarylalkanes as building blocks for drug discovery, as well as the straightforward and modular sequence to prepare the pyridylidene‐Cu‐complexes, makes this catalyst and it applications attractive for chemical synthesis. Furthermore, chiral variants of the pyridylidene‐Cu‐complexes have been prepared and utilized in the enantioselective arylboration of E‐alkenes, further demonstrating the value and potential of this class of catalysts.
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Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N‐Heterocycles
Abstract Two catalytic systems have been developed for the arylboration of endocyclic enecarbamates to deliver synthetically versatile borylated saturated N‐heterocycles 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/Pd‐system, 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.
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- Award ID(s):
- 1920026
- PAR ID:
- 10375922
- Publisher / Repository:
- Wiley Blackwell (John Wiley & Sons)
- Date Published:
- Journal Name:
- Angewandte Chemie International Edition
- Volume:
- 61
- Issue:
- 46
- ISSN:
- 1433-7851
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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