Prospects and challenges for nitrogen-atom transfer catalysis

Cosio, Mario N.; Powers, David C.

doi:10.1038/s41570-023-00482-1

Prospects and challenges for nitrogen-atom transfer catalysis

Journal Article · Thu Apr 13 00:00:00 UTC 2023 · Nature Reviews Chemistry

DOI:https://doi.org/10.1038/s41570-023-00482-1· OSTI ID:2433868

Cosio, Mario N. ^[1]; ^[2]

Texas A&M University, College Station, TX (United States); Texas A&M University
Texas A&M University, College Station, TX (United States)

Incorporation of nitrogen-based functional groups can profoundly impact the chemical and physical properties of organic small molecules. One-step conversion of C–H bonds to C–N bonds via C–H amination promises to streamline the synthesis of nitrogen-containing compounds. In pursuit of this promise, nitrogen-group transfer (NGT) from metal nitrenes (i.e., ligand supported M–NR complexes) has been the focus of intense research and development. In contrast, potentially complementary nitrogen-atom transfer (NAT) chemistry, in which a terminal metal nitride (i.e., ligand-supported M–N complex) engages with a C–H bond, is undeveloped. While the earliest examples of stoichiometric NAT chemistry were reported 25 years ago, catalytic protocols are only now beginning to emerge. Furthermore, we summarize the current state-of-the-art in NAT chemistry and discuss opportunities and challenges for the development of NAT catalysis as a platform for incorporation of nitrogen into organic small molecules. Specifically, we 1) highlight the synthetic complementarity of NGT and NAT chemistry, 2) discuss critical aspects of nitride electronic structure that dictate the philicity of supported metal atom, 3) examine the characteristic reactivity of metal nitrides towards substrate functionalization reactions, and 4) present emerging strategies and remaining obstacles to harnessing NAT for selective, catalytic nitrogenation of unfunctionalized organic small molecules.

View Accepted Manuscript (DOE)

Research Organization:: Texas A&M University, College Station, TX (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES); Welch Foundation

Grant/Contract Number:: SC0018977

OSTI ID:: 2433868

Alternate ID(s):: OSTI ID: 2420892

Journal Information:: Nature Reviews Chemistry, Journal Name: Nature Reviews Chemistry Journal Issue: 6 Vol. 7; ISSN 2397-3358

Publisher:: Springer NatureCopyright Statement

Country of Publication:: United States

Language:: English

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