Synlett 2024; 35(08): 851-861
DOI: 10.1055/s-0042-1751519
account
Special Issue dedicated to Keith Fagnou

Nickel-Catalyzed sp3 C–H Activation

,
Shangyu Li
,
Ramon Arora
,
Bijan Mirabi
,
Mark Lautens
We thank the University of Toronto (UofT), the Natural Science and Engineering Research Council (NSERC), Alphora Research Inc. and Kennarshore Inc. for financial support. C. E. J. thanks the Ontario government for an OGS fellowship. R. A. thanks NSERC for a CGS-D fellowship. B. M. thanks NSERC for a CGS-D fellowship.


Abstract

Base metal catalyzed C–H activation represents a highly atom economic method to access functionalized molecules. This Account will focus on Ni-catalyzed C–H activation of sp3-hybridized carbon atoms with a particular focus on mechanism, recent applications, challenges, and outlook in this area. This Account will primarily focus on recent mechanistic work from 2017–2023.
1 Base Metal C–H Activation

2 Nickel-Catalyzed sp3 C–H activation

3 Differences between Ni and Pd

4 Mechanistic Considerations

5 Elementary Steps

6 Directed sp3 C–H Activation

7 Choice of Directing Group

8 Primary C–H Activation

9 Secondary C–H Activation

10 Tertiary C–H Activation

11 Conclusion and Outlook



Publication History

Received: 06 September 2023

Accepted after revision: 04 October 2023

Article published online:
24 November 2023

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