Measuring the Relative Reactivity of the Carbon–Hydrogen Bonds of Alkanes as Nucleophiles

Andrea Olmos; Riccardo Gava; Bárbara Noverges; Delia Bellezza; Kane Jacob; Maria Besora; W. M.Chamil Sameera; Michel Etienne; Feliu Maseras; Gregorio Asensio; Ana Caballero; Pedro J. Pérez

doi:10.1002/anie.201807448

Measuring the Relative Reactivity of the Carbon–Hydrogen Bonds of Alkanes as Nucleophiles

Andrea Olmos, Riccardo Gava, Bárbara Noverges, Delia Bellezza, Kane Jacob, Maria Besora, W. M.Chamil Sameera, Michel Etienne, Feliu Maseras, Gregorio Asensio, Ana Caballero, Pedro J. Pérez

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© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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 in situ 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.

Idioma original	Anglès
Pàgines (de-a)	13848-13852
Revista	Angewandte Chemie - International Edition
Volum	57
DOIs	https://doi.org/10.1002/anie.201807448
Estat de la publicació	Publicada - 15 d’oct. 2018

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title = "Measuring the Relative Reactivity of the Carbon–Hydrogen Bonds of Alkanes as Nucleophiles",

abstract = "{\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim 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 in situ 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.",

keywords = "alkanes, C−H bond functionalization, electrophilicity, metal carbene complexes, nucleophilicity",

author = "Andrea Olmos and Riccardo Gava and B{\'a}rbara Noverges and Delia Bellezza and Kane Jacob and Maria Besora and Sameera, \{W. M.Chamil\} and Michel Etienne and Feliu Maseras and Gregorio Asensio and Ana Caballero and P{\'e}rez, \{Pedro J.\}",

year = "2018",

month = oct,

day = "15",

doi = "10.1002/anie.201807448",

language = "English",

volume = "57",

pages = "13848--13852",

journal = "Angewandte Chemie - International Edition",

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TY - JOUR

T1 - Measuring the Relative Reactivity of the Carbon–Hydrogen Bonds of Alkanes as Nucleophiles

AU - Olmos, Andrea

AU - Gava, Riccardo

AU - Noverges, Bárbara

AU - Bellezza, Delia

AU - Jacob, Kane

AU - Besora, Maria

AU - Sameera, W. M.Chamil

AU - Etienne, Michel

AU - Maseras, Feliu

AU - Asensio, Gregorio

AU - Caballero, Ana

AU - Pérez, Pedro J.

PY - 2018/10/15

Y1 - 2018/10/15

N2 - © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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 in situ 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.

AB - © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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 in situ 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.

KW - alkanes

KW - C−H bond functionalization

KW - electrophilicity

KW - metal carbene complexes

KW - nucleophilicity

UR - https://www.scopus.com/pages/publications/85052487106

U2 - 10.1002/anie.201807448

DO - 10.1002/anie.201807448

M3 - Article

C2 - 30015368

SN - 1433-7851

VL - 57

SP - 13848

EP - 13852

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

ER -

Measuring the Relative Reactivity of the Carbon–Hydrogen Bonds of Alkanes as Nucleophiles

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