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• W2911260676 abstract "Abstract Undirected C(sp 3 )−H functionalization reactions often follow site‐selectivity patterns that mirror the corresponding C−H bond dissociation energies (BDEs). This often results in the functionalization of weaker tertiary C−H bonds in the presence of stronger secondary and primary bonds. An important, contemporary challenge is the development of catalyst systems capable of selectively functionalizing stronger primary and secondary C−H bonds over tertiary and benzylic C−H sites. Herein, we report a Cu catalyst that exhibits a high degree of primary and secondary over tertiary C−H bond selectivity in the amidation of linear and cyclic hydrocarbons with aroyl azides ArC(O)N 3 . Mechanistic and DFT studies indicate that C−H amidation involves H‐atom abstraction from R‐H substrates by nitrene intermediates [Cu](κ 2 ‐ N , O ‐NC(O)Ar) to provide carbon‐based radicals R . and copper(II)amide intermediates [Cu II ]‐NHC(O)Ar that subsequently capture radicals R . to form products R‐NHC(O)Ar. These studies reveal important catalyst features required to achieve primary and secondary C−H amidation selectivity in the absence of directing groups." @default.
• W2911260676 created "2019-02-21" @default.
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• W2911260676 date "2019-02-07" @default.
• W2911260676 modified "2023-10-11" @default.
• W2911260676 title "Copper‐Catalyzed C(sp ³ )−H Amidation: Sterically Driven Primary and Secondary C−H Site‐Selectivity" @default.
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• W2911260676 doi "https://doi.org/10.1002/anie.201810556" @default.
• W2911260676 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30675976" @default.
• W2911260676 hasPublicationYear "2019" @default.
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