Transition-metal-free radical relay cyclization of vinyl azides with 1,4-dihydropyridines involving a 1,5-hydrogen-atom transfer: access to α-tetralone scaffolds

2020 ◽  
Vol 7 (22) ◽  
pp. 3638-3647
Author(s):  
Yangzhen Liao ◽  
Yu Ran ◽  
Guijun Liu ◽  
Peijun Liu ◽  
Xiaozu Liu
Keyword(s):  
Free Radical ◽  
Hydrogen Atom ◽  
Transition Metal ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Metal Free ◽  
Vinyl Azides

The remote C(sp3)–H functionalization enabled by a radical-mediated 1,5-hydrogen-atom transfer (HAT) process using vinyl azides and 1,4-dihydropyridines as precursors has been described.

Transition-Metal-Free C(sp3)–H Coupling of Cycloalkanes Enabled by Single-Electron Transfer and Hydrogen Atom Transfer

2021 ◽  
Vol 23 (5) ◽  
pp. 1714-1719
Author(s):  
Linlin Zhang ◽  
Zhengfen Liu ◽  
Xun Tian ◽  
Yujin Zi ◽  
Shengzu Duan ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Hydrogen Atom ◽  
Transition Metal ◽  
Hydrogen Atom Transfer ◽  
Single Electron ◽  
Atom Transfer ◽  
Single Electron Transfer ◽  
Metal Free

Direct Cyclization of Alkenyl Thioester via Transition Metal‐hydrogen Atom Transfer/radical‐polar Crossover Mechanism

2019 ◽  
Author(s):  
Shiori Date ◽  
Kensei Hamasaki ◽  
Karen Sunagawa ◽  
Hiroki Koyama ◽  
Chikayoshi Sebe ◽  
...  
Keyword(s):  
Natural Products ◽  
Hydrogen Atom ◽  
Transition Metal ◽  
Hydrogen Atom Transfer ◽  
Synthetic Method ◽  
Atom Transfer ◽  
Reaction Conditions ◽  
Hydride Hydrogen ◽  
Sulfur Heterocycles ◽  
One Step

<div>We report here a catalytic, Markovnikov selective, and scalable synthetic method for the synthesis of saturated sulfur heterocycles, which are found in the structures of pharmaceuticals and natural products, in one step from an alkenyl thioester. Unlike a potentially labile alkenyl thiol, an alkenyl thioester is stable and easy to prepare. The powerful Co catalysis via a cobalt hydride hydrogen atom transfer and radical-polar crossover mechanism enabled simultaneous cyclization and deprotection. The substrate scope was expanded by the extensive optimization of the reaction conditions and tuning of the thioester unit.</div>

scholarly journals Trends in Ground-State Entropies for Transition Metal Based Hydrogen Atom Transfer Reactions

2009 ◽  
Vol 131 (12) ◽  
pp. 4335-4345 ◽  
Author(s):  
Elizabeth A. Mader ◽  
Virginia W. Manner ◽  
Todd F. Markle ◽  
Adam Wu ◽  
James A. Franz ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Transition Metal ◽  
Ground State ◽  
Hydrogen Atom Transfer ◽  
Transfer Reactions ◽  
Atom Transfer ◽  
Atom Transfer Reactions

scholarly journals Syntheses of Trifluoroethylated N-Heterocycles from Vinyl Azides and Togni’s Reagent Involving 1,n-Hydrogen-Atom Transfer Reactions

2020 ◽  
Vol 22 (12) ◽  
pp. 4766-4770 ◽  
Author(s):  
Steven Terhorst ◽  
Deo Prakash Tiwari ◽  
Daniela Meister ◽  
Benedict Petran ◽  
Kari Rissanen ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Hydrogen Atom Transfer ◽  
Transfer Reactions ◽  
Atom Transfer ◽  
Atom Transfer Reactions ◽  
Vinyl Azides

scholarly journals Light-enabled metal-free pinacol coupling by hydrazine

2019 ◽  
Vol 10 (47) ◽  
pp. 10937-10943 ◽  
Author(s):  
Zihang Qiu ◽  
Hanh D. M. Pham ◽  
Jianbin Li ◽  
Chen-Chen Li ◽  
Durbis J. Castillo-Pazos ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Metallic Hydrogen ◽  
Metal Free ◽  
Pinacol Coupling

A light-driven pinacol coupling protocol without any metals, but with N2H4 as a clean non-metallic hydrogen-atom-transfer (HAT) reductant was described.

Direct Cyclization of Alkenyl Thioester via Transition Metal‐hydrogen Atom Transfer/radical‐polar Crossover Mechanism

2019 ◽  
Author(s):  
Shiori Date ◽  
Kensei Hamasaki ◽  
Karen Sunagawa ◽  
Hiroki Koyama ◽  
Chikayoshi Sebe ◽  
...  
Keyword(s):  
Natural Products ◽  
Hydrogen Atom ◽  
Transition Metal ◽  
Hydrogen Atom Transfer ◽  
Synthetic Method ◽  
Atom Transfer ◽  
Reaction Conditions ◽  
Hydride Hydrogen ◽  
Sulfur Heterocycles ◽  
One Step

<div>We report here a catalytic, Markovnikov selective, and scalable synthetic method for the synthesis of saturated sulfur heterocycles, which are found in the structures of pharmaceuticals and natural products, in one step from an alkenyl thioester. Unlike a potentially labile alkenyl thiol, an alkenyl thioester is stable and easy to prepare. The powerful Co catalysis via a cobalt hydride hydrogen atom transfer and radical-polar crossover mechanism enabled simultaneous cyclization and deprotection. The substrate scope was expanded by the extensive optimization of the reaction conditions and tuning of the thioester unit.</div>

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