Transition-metal-free radical cleavage of a hydrazonyl N–S bond: tosyl radical-initiated cascade C(sp3)–OAr cleavage, sulfonyl rearrangement and atropisomeric cyclopropanation

2018 ◽  
Vol 5 (24) ◽  
pp. 3567-3573 ◽  
Author(s):  
Yao-Zhong Chen ◽  
Teng Liu ◽  
Jie Zhu ◽  
Hui Zhang ◽  
Lei Wu
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Potassium Carbonate ◽  
Coupling Reaction ◽  
Metal Free ◽  
Radical Cleavage

Combination of 1,10-phenanthroline and potassium carbonate enables a radical cleavage of a hydrazonyl N–S bond, allowing a coupling reaction of N-tosylhydrazone and phosphinyl allene via cascade C–O cleavage, sulfonyl rearrangement and atropisomeric cyclopropanation.

(Diacetoxyiodo)benzene-Mediated Transition-Metal-Free Amination of C(sp3)–H Bonds Adjacent to Heteroatoms with Azoles: Synthesis of N-Alkylated Azoles

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2432-2436 ◽  
Author(s):  
Can Jin ◽  
Weike Su ◽  
Bin Sun ◽  
Zhiyang Yan
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Coupling Reaction ◽  
Metal Catalyst ◽  
Metal Free ◽  
Alternative Method ◽  
Dehydrogenative Coupling ◽  
Wide Range ◽  
Ready Access

A novel PhI(OAc)2-mediated cross-dehydrogenative coupling reaction of α-C(sp3)–H bonds adjacent to a hetero atom with various azoles has been developed, which provides an alternative method for constructing C–N bonds with high atom efficiency. This new protocol requires no metal catalyst and it provides ready access to a wide range of N-alkylated azole derivatives in moderate to excellent yields by using commercially available PhI(OAc)2 as the sole oxidant. Furthermore, the method is effective on a gram scale, which highlights the practicality of this transformation. The result of radical-captured experiments indicated that the transformation might involve a free-radical pathway.

Transition metal free intramolecular selective oxidative C(sp3)–N coupling: synthesis of N-aryl-isoindolinones from 2-alkylbenzamides

2015 ◽  
Vol 51 (7) ◽  
pp. 1371-1374 ◽  
Author(s):  
Ajay Verma ◽  
Saket Patel ◽  
Meenakshi Meenakshi ◽  
Amit Kumar ◽  
Abhimanyu Yadav ◽  
...  
Keyword(s):  
Transition Metal ◽  
Potassium Carbonate ◽  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Metal Free ◽  
Oxidative Coupling Reaction ◽  
Butyl Peroxide

A transition metal-free intramolecular selective oxidative coupling reaction of C(sp3)–H and N–H bonds has been presented utilizing iodine, potassium carbonate and di-tert-butyl peroxide in acetonitrile at 110–140 °C.

Potassium carbonate-mediated tandem C–S and C–N coupling reaction for the synthesis of phenothiazines under transition-metal-free and ligand-free conditions

RSC Advances ◽  
2016 ◽  
Vol 6 (29) ◽  
pp. 24257-24260 ◽  
Author(s):  
San Wu ◽  
Wei-Ye Hu ◽  
Song-Lin Zhang
Keyword(s):  
Transition Metal ◽  
Potassium Carbonate ◽  
Coupling Reaction ◽  
Metal Catalyst ◽  
Phenothiazine Derivatives ◽  
Transition Metal Catalyst ◽  
Metal Free ◽  
Efficient Approach ◽  
Ligand Free

A potassium carbonate-mediated tandem coupling reaction for the synthesis of phenothiazines is described. This protocol affords an efficient approach for the construction of phenothiazine derivatives without the need for addition of transition-metal catalyst or ligand.

Deaminative carbonylative thioesterification of activated alkylamines with thiophenols under transition-metal-free conditions

2021 ◽  
Author(s):  
Fengqian Zhao ◽  
Xiao-Feng Wu
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Metal Free

A transition-metal-free radical carbonylation of activated alkylamines with thiophenols has been successfully developed. Various thioesters were selectively produced with moderate to good yields.

A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

2021 ◽  
Author(s):  
Tao Fan ◽  
Yan Liu ◽  
Caina Jiang ◽  
Yanli Xu ◽  
Yan-Yan Chen
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Cascade Reaction ◽  
Phosphine Oxides ◽  
Metal Free ◽  
Mild Conditions ◽  
Xanthene Derivatives ◽  
Reaction Proceeds ◽  
Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

ChemInform Abstract: A Transition-Metal-Free Cross-Coupling Reaction of Allylic Bromides with Aryl- and Vinylboronic Acids.

ChemInform ◽  
2012 ◽  
Vol 43 (33) ◽  
pp. no-no
Author(s):  
Mitsuhiro Ueda ◽  
Kota Nishimura ◽  
Ryo Kashima ◽  
Ilhyong Ryu
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Free ◽  
Cross Coupling Reaction

scholarly journals Transition-Metal-Free Radical C(sp3)–C(sp2) and C(sp3)–C(sp3) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners

2017 ◽  
Vol 139 (45) ◽  
pp. 16327-16333 ◽  
Author(s):  
Minyan Li ◽  
Simon Berritt ◽  
Lucas Matuszewski ◽  
Guogang Deng ◽  
Ana Pascual-Escudero ◽  
...  
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Electron Donors ◽  
Metal Free
Sign in / Sign up

Export Citation Format

Share Document