Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 42, Pages 13848-13852Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807448
Keywords
alkanes; C-H bond functionalization; electrophilicity; metal carbene complexes; nucleophilicity
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Funding
- MINECO [CTQ2014-52769-C03-01, CTQ2014-52769-C03-02, CTQ2017-82893-C2-1-R, CTQ2014-62234-EXP, CTQ2015-73693-JIN, CTQ2017-87792-R]
- Severo Ochoa Excellence Accreditation [SEV-2013-0319]
- Red Intecat [CTQ2016-81923-REDC]
- Junta de Andalucia [P12-FQM-1765]
- MINECO
- Juan delaCierva fellowship
- MEC
- CNRS
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We report quantitative measurements of the relative reactivities of a series of C-H bonds of gaseous or liquid CnH2n+2 alkanes (n = 1-8, 29 different C-H bonds) towards insitu generated electrophiles (copper, silver, and rhodium carbenes), with methane as the reference. This strategy surpasses the drawback of previous model reactions of alkanes with strong electrophiles suffering from C-C cleavage processes, which precluded direct comparison of the relative reactivities of alkane C-H bonds.
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