Ni-Catalyzed Reductive Coupling of Alkyl Acids with Unactivated Tertiary Alkyl and Glycosyl Halides

2014 ◽  
Vol 136 (50) ◽  
pp. 17645-17651 ◽  
Author(s):  
Chenglong Zhao ◽  
Xiao Jia ◽  
Xuan Wang ◽  
Hegui Gong
Keyword(s):  
Reductive Coupling ◽  
Tertiary Alkyl

Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides

2018 ◽  
Vol 140 (43) ◽  
pp. 14490-14497 ◽  
Author(s):  
Xuan Wang ◽  
Guobin Ma ◽  
Yu Peng ◽  
Chloe E. Pitsch ◽  
Brenda J. Moll ◽  
...  
Keyword(s):  
Alkyl Halides ◽  
Reductive Coupling ◽  
Aryl Iodides ◽  
Tertiary Alkyl

Formation of allylated quaternary carbon centers via C–O/C–O bond fragmentation of oxalates and allyl carbonates

2020 ◽  
Vol 56 (3) ◽  
pp. 454-457 ◽  
Author(s):  
Haifeng Chen ◽  
Yang Ye ◽  
Weiqi Tong ◽  
Jianhui Fang ◽  
Hegui Gong
Keyword(s):  
Fragmentation Process ◽  
Reductive Coupling ◽  
Quaternary Carbon ◽  
Carbon Centers ◽  
Tertiary Alkyl

Fe-Promoted reductive coupling of tertiary alkyl oxalates with allylic carbonates enables the formation of all C(sp3)–quaternary carbon centers via a double C–O bond fragmentation process.

An extension of nickel-catalyzed reductive coupling between tertiary alkyl halides with allylic carbonates

Tetrahedron ◽  
2018 ◽  
Vol 74 (39) ◽  
pp. 5651-5658 ◽  
Author(s):  
Yingying Yu ◽  
Haifeng Chen ◽  
Qun Qian ◽  
Ken Yao ◽  
Hegui Gong
Keyword(s):  
Alkyl Halides ◽  
Reductive Coupling ◽  
Tertiary Alkyl

ChemInform Abstract: Ni-Catalyzed Reductive Coupling of Alkyl Acids with Unactivated Tertiary Alkyl and Glycosyl Halides.

ChemInform ◽  
2015 ◽  
Vol 46 (21) ◽  
pp. no-no
Author(s):  
Chenglong Zhao ◽  
Xiao Jia ◽  
Xuan Wang ◽  
Hegui Gong
Keyword(s):  
Reductive Coupling ◽  
Tertiary Alkyl

Nickel-Catalyzed Reductive Coupling of Aryl Bromides with Tertiary Alkyl Halides

2015 ◽  
Vol 137 (36) ◽  
pp. 11562-11565 ◽  
Author(s):  
Xuan Wang ◽  
Shulin Wang ◽  
Weichao Xue ◽  
Hegui Gong
Keyword(s):  
Alkyl Halides ◽  
Reductive Coupling ◽  
Aryl Bromides ◽  
Tertiary Alkyl

ChemInform Abstract: Nickel-Catalyzed Reductive Coupling of Aryl Bromides with Tertiary Alkyl Halides.

ChemInform ◽  
2016 ◽  
Vol 47 (9) ◽  
pp. no-no
Author(s):  
Xuan Wang ◽  
Shulin Wang ◽  
Weichao Xue ◽  
Hegui Gong
Keyword(s):  
Alkyl Halides ◽  
Reductive Coupling ◽  
Aryl Bromides ◽  
Tertiary Alkyl

scholarly journals Amine synthesis via iron-catalysed reductive coupling of nitroarenes with alkyl halides

2016 ◽  
Vol 7 (1) ◽  
Author(s):  
Chi Wai Cheung ◽  
Xile Hu
Keyword(s):  
Organic Molecules ◽  
Functional Group ◽  
Iron Catalyst ◽  
Alkyl Halides ◽  
Mechanistic Study ◽  
Reductive Coupling ◽  
Alkyl Radicals ◽  
Aryl Amines ◽  
Tertiary Alkyl ◽  
General Method

Abstract (Hetero)Aryl amines, an important class of organic molecules in medicinal chemistry, are most commonly synthesized from anilines, which are in turn synthesized by hydrogenation of nitroarenes. Amine synthesis directly from nitroarenes is attractive due to improved step economy and functional group compatibility. Despite these potential advantages, there is yet no general method for the synthesis of (hetero)aryl amines by carbon–nitrogen cross-coupling of nitroarenes. Here we report the reductive coupling of nitroarenes with alkyl halides to yield (hetero)aryl amines. A simple iron catalyst enables the coupling with numerous primary, secondary and tertiary alkyl halides. Broad scope and high functional group tolerance are demonstrated. Mechanistic study suggests that nitrosoarenes and alkyl radicals are involved as intermediates. This new C–N coupling method provides general and step-economical access to aryl amines.

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