The Alkylation and Reduction of Heteroarenes with Alcohols Using Photoredox Catalyzed Hydrogen Atom Transfer via Chlorine Atom Generation

2019 ◽  
Vol 2020 (10) ◽  
pp. 1453-1458 ◽  
Author(s):  
Montserrat Zidan ◽  
Avery O. Morris ◽  
Terry McCallum ◽  
Louis Barriault
Keyword(s):  
Hydrogen Atom ◽  
Chlorine Atom ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer

Hydrogen Atom Transfer Reactions via Photoredox Catalyzed Chlorine Atom Generation

2018 ◽  
Vol 57 (48) ◽  
pp. 15664-15669 ◽  
Author(s):  
Samantha Rohe ◽  
Avery O. Morris ◽  
Terry McCallum ◽  
Louis Barriault
Keyword(s):  
Hydrogen Atom ◽  
Chlorine Atom ◽  
Hydrogen Atom Transfer ◽  
Transfer Reactions ◽  
Atom Transfer ◽  
Atom Transfer Reactions

Hydrogen Atom Transfer Reactions via Photoredox Catalyzed Chlorine Atom Generation

2018 ◽  
Vol 130 (48) ◽  
pp. 15890-15895 ◽  
Author(s):  
Samantha Rohe ◽  
Avery O. Morris ◽  
Terry McCallum ◽  
Louis Barriault
Keyword(s):  
Hydrogen Atom ◽  
Chlorine Atom ◽  
Hydrogen Atom Transfer ◽  
Transfer Reactions ◽  
Atom Transfer ◽  
Atom Transfer Reactions

scholarly journals Frontispiz: Hydrogen Atom Transfer Reactions via Photoredox Catalyzed Chlorine Atom Generation

2018 ◽  
Vol 130 (48) ◽  
Author(s):  
Samantha Rohe ◽  
Avery O. Morris ◽  
Terry McCallum ◽  
Louis Barriault
Keyword(s):  
Hydrogen Atom ◽  
Chlorine Atom ◽  
Hydrogen Atom Transfer ◽  
Transfer Reactions ◽  
Atom Transfer ◽  
Atom Transfer Reactions

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>

Catalytic Synthesis of Cyclic Guanidines via Hydrogen Atom Transfer and Radical-Polar Crossover

2020 ◽  
Author(s):  
Shunya Ohuchi ◽  
Hiroki Koyama ◽  
Hiroki Shigehisa
Keyword(s):  
Hydrogen Atom ◽  
Functional Group ◽  
Hydrogen Atom Transfer ◽  
Catalytic Synthesis ◽  
Membered Ring ◽  
Biologically Active ◽  
Atom Transfer ◽  
Powerful Method ◽  
Protective Groups ◽  
The Common

A catalytic synthesis of cyclic guanidines, which are found in many biologically active compounds and natu-ral products, was developed, wherein transition-metal hydrogen atom transfer and radical-polar crossover were employed. This mild and functional-group tolerant process enabled the cyclization of alkenyl guanidines bearing common protective groups, such as Cbz and Boc. This powerful method not only provided the common 5- and 6-membered rings but also an unusual 7-membered ring. The derivatization of the products afforded various heterocycles. We also investigated the se-lective cyclization of mono-protected or hetero-protected (TFA and Boc) alkenyl guanidines and their further derivatiza-tions.

Sulfamides Direct Radical-Mediated Chlorination of Aliphatic C–H Bonds

2019 ◽  
Author(s):  
Melanie Short ◽  
Mina Shehata ◽  
Matthew Sanders ◽  
Jennifer Roizen
Keyword(s):  
Hydrogen Atom ◽  
Transfer Reaction ◽  
Hydrogen Atom Transfer ◽  
Chain Propagation ◽  
Propagation Mechanism ◽  
Atom Transfer ◽  
Radical Chain ◽  
Radical Intermediates ◽  
Transfer Processes ◽  
Unusual Position

Sulfamides guide intermolecular chlorine transfer to gamma-C(sp<sup>3</sup>) centers. This unusual position-selectivity arises because accessed sulfamidyl radical intermediates engage in otherwise rare 1,6-hydrogen-atom transfer processes. The disclosed chlorine-transfer reaction relies on a light-initiated radical chain-propagation mechanism to oxidize C(sp<sup>3</sup>)-H bonds.

Sulfamides Direct Radical-Mediated Chlorination of Aliphatic C–H Bonds

2019 ◽  
Author(s):  
Melanie Short ◽  
Mina Shehata ◽  
Matthew Sanders ◽  
Jennifer Roizen
Keyword(s):  
Hydrogen Atom ◽  
Transfer Reaction ◽  
Hydrogen Atom Transfer ◽  
Chain Propagation ◽  
Propagation Mechanism ◽  
Atom Transfer ◽  
Radical Chain ◽  
Radical Intermediates ◽  
Transfer Processes ◽  
Unusual Position

Sulfamides guide intermolecular chlorine transfer to gamma-C(sp<sup>3</sup>) centers. This unusual position-selectivity arises because accessed sulfamidyl radical intermediates engage in otherwise rare 1,6-hydrogen-atom transfer processes. The disclosed chlorine-transfer reaction relies on a light-initiated radical chain-propagation mechanism to oxidize C(sp<sup>3</sup>)-H bonds.

Sign in / Sign up

Export Citation Format

Share Document