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

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

scholarly journals Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides

2020 ◽  
Author(s):  
José Augusto Forni ◽  
NENAD MICIC ◽  
Timothy Connell ◽  
GEETHIKA WERAGODA ◽  
Anastasios Polyzos
Keyword(s):  
Natural Products ◽  
Late Stage ◽  
Aromatic Amines ◽  
Functional Group ◽  
Alkyl Halides ◽  
Catalytic Cycle ◽  
Aryl Bromides ◽  
Alkyl Iodides ◽  
Tertiary Alkyl

<p>We report a new visible light-mediated carbonylative amidation of aryl, heteroaryl and alkyl halides. A tandem catalytic cycle of [Ir(ppy)<sub>2</sub>(dtb-bpy)]<sup>+</sup> generates a potent iridium photoreductant via a second catalytic cycle in the presence of DIPEA which productively engages aryl bromides, iodides and even chlorides as well as primary, secondary and tertiary alkyl iodides. The versatility of the in-situ generated catalyst is illustrated by compatibility with aliphatic and aromatic amines, high functional group tolerance and the late-stage amidation of complex natural products. </p>

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

scholarly journals Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides

2020 ◽  
Author(s):  
José Augusto Forni ◽  
NENAD MICIC ◽  
Timothy Connell ◽  
GEETHIKA WERAGODA ◽  
Anastasios Polyzos
Keyword(s):  
Natural Products ◽  
Late Stage ◽  
Aromatic Amines ◽  
Functional Group ◽  
Alkyl Halides ◽  
Catalytic Cycle ◽  
Aryl Bromides ◽  
Alkyl Iodides ◽  
Tertiary Alkyl

<p>We report a new visible light-mediated carbonylative amidation of aryl, heteroaryl and alkyl halides. A tandem catalytic cycle of [Ir(ppy)<sub>2</sub>(dtb-bpy)]<sup>+</sup> generates a potent iridium photoreductant via a second catalytic cycle in the presence of DIPEA which productively engages aryl bromides, iodides and even chlorides as well as primary, secondary and tertiary alkyl iodides. The versatility of the in-situ generated catalyst is illustrated by compatibility with aliphatic and aromatic amines, high functional group tolerance and the late-stage amidation of complex natural products. </p>

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.

scholarly journals Tertiary alkyl halides as growth activator and inhibitor for novel atomic layer deposition of low resistive titanium nitride

AIP Advances ◽  
2021 ◽  
Vol 11 (1) ◽  
pp. 015218
Author(s):  
Changbong Yeon ◽  
Jaesun Jung ◽  
Hyeran Byun ◽  
Kok Chew Tan ◽  
Taeho Song ◽  
...  
Keyword(s):  
Atomic Layer Deposition ◽  
Titanium Nitride ◽  
Atomic Layer ◽  
Alkyl Halides ◽  
Layer Deposition ◽  
Tertiary Alkyl

scholarly journals Mizoroki–Heck type reactions and synthesis of 1,4-dicarbonyl compounds by heterogeneous organic semiconductor photocatalysis

2021 ◽  
Vol 23 (5) ◽  
pp. 2017-2024
Author(s):  
Jagadish Khamrai ◽  
Saikat Das ◽  
Aleksandr Savateev ◽  
Markus Antonietti ◽  
Burkhard König
Keyword(s):  
Visible Light ◽  
Vinyl Acetate ◽  
Organic Semiconductor ◽  
Alkyl Halides ◽  
Visible Light Photocatalysis ◽  
Dicarbonyl Compounds ◽  
Semiconductor Photocatalysis ◽  
Type Coupling ◽  
Styrene Derivatives ◽  
Tertiary Alkyl

We report the synthesis of 1,4-dicarbonyl compounds and substituted alkenes (Mizoroki–Heck type coupling) starting from secondary and tertiary alkyl halides and vinyl acetate or styrene derivatives using visible-light photocatalysis.

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