Photoredox-Mediated Minisci-type Alkylation of N-Heteroarenes with Alkanes with High Methylene Selectivity

ACS Catalysis ◽  
2018 ◽  
Vol 8 (12) ◽  
pp. 11847-11853 ◽  
Author(s):  
Guo-Xing Li ◽  
Xiafei Hu ◽  
Gang He ◽  
Gong Chen
Keyword(s):  
Methylene Selectivity

scholarly journals Pd(II)-Catalyzed Synthesis of Benzocyclobutenes by β-Methylene-Selective C(sp3)‒H Arylation with a Transient Directing Group

2021 ◽  
Author(s):  
Philip Provencher ◽  
John Hoskin ◽  
Jonathan Wong ◽  
Xiangyang Chen ◽  
Jin-Quan Yu ◽  
...  
Keyword(s):  
Reaction Conditions ◽  
Methylene Selectivity ◽  
Directing Group

Methylene-selective C‒H functionalization is a significant hurdle that remains to be addressed in the field of Pd(II) cataly-sis. In this paper we report a Pd(II) catalyzed synthesis of benzocyclobutenes by methylene-selective C(sp3)‒H arylation of ketones using a transient directing group. The reaction utilizes glycine as a transient directing group and an electron poor pyridone ligand which is expected to promote concerted metallation deprotonation, but also controls methylene selectivity by intimate interactions with the substrate. These reaction conditions are shown to be highly selective for in-tramolecular methylene C(sp3)‒H arylation, and thus enable sequential C(sp3)‒H functionalization.

Methylene selectivity in microemulsion liquid chromatography

2015 ◽  
Vol 70 (4) ◽  
pp. 175-182 ◽  
Author(s):  
L. S. Sokolova ◽  
A. A. Derbina ◽  
E. B. Pashkova ◽  
A. V. Pirogov ◽  
O. A. Shpigun
Keyword(s):  
Liquid Chromatography ◽  
Methylene Selectivity ◽  
Microemulsion Liquid Chromatography

scholarly journals Pd(II)-Catalyzed Synthesis of Benzocyclobutenes by β-Methylene-Selective C(sp3)‒H Arylation with a Transient Directing Group

2021 ◽  
Author(s):  
Philip Provencher ◽  
John Hoskin ◽  
Jonathan Wong ◽  
Xiangyang Chen ◽  
Jin-Quan Yu ◽  
...  
Keyword(s):  
Reaction Conditions ◽  
Methylene Selectivity ◽  
Directing Group

Methylene-selective C‒H functionalization is a significant hurdle that remains to be addressed in the field of Pd(II) cataly-sis. In this paper we report a Pd(II) catalyzed synthesis of benzocyclobutenes by methylene-selective C(sp3)‒H arylation of ketones using a transient directing group. The reaction utilizes glycine as a transient directing group and an electron poor pyridone ligand which is expected to promote concerted metallation deprotonation, but also controls methylene selectivity by intimate interactions with the substrate. These reaction conditions are shown to be highly selective for in-tramolecular methylene C(sp3)‒H arylation, and thus enable sequential C(sp3)‒H functionalization.

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