A metal-free biaryl coupling reaction activated by a sulfonium salt

2018 ◽  
Vol 5 (22) ◽  
pp. 3219-3225 ◽  
Author(s):  
Kazuhiro Higuchi ◽  
Takuhiro Tago ◽  
Yusuke Kokubo ◽  
Motoki Ito ◽  
Masanori Tayu ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Sulfonium Salt ◽  
One Pot ◽  
Metal Free ◽  
Trifluoromethanesulfonic Anhydride ◽  
Biaryl Coupling ◽  
Aryl Ethers

A metal-free biaryl coupling reaction of phenol or aryl ethers mediated by a sulfonium salt formed from diphenyl sulfoxide and trifluoromethanesulfonic anhydride has been developed. The method is a rapid, one-pot reaction, leaving no traces of the sulfonium moiety in the product.

scholarly journals Sequential In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reactions using bromopropargyl aryl ethers and amines

2017 ◽  
Vol 4 (4) ◽  
pp. 500-505 ◽  
Author(s):  
Lorena Alonso-Marañón ◽  
Luis A. Sarandeses ◽  
M. Montserrat Martínez ◽  
José Pérez Sestelo
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
One Pot ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Aryl Ethers

A sequential one-pot In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reaction using bromopropargyl aryl ethers and amines has been developed.

Metal-free Oxidative Cross-Coupling Reaction of Aromatic Compounds Containing Heteroatoms

Synlett ◽  
2017 ◽  
Vol 28 (14) ◽  
pp. 1680-1694 ◽  
Author(s):  
Koji Morimoto ◽  
Toshifumi Dohi ◽  
Yasuyuki Kita
Keyword(s):  
Aromatic Compounds ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Hypervalent Iodine ◽  
Coupling Reactions ◽  
Heteroaromatic Compounds ◽  
Metal Free ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Biaryl Coupling

The biaryl unit containing a heteroatom is a key structure in a large number of natural products and π-conjugated organic systems. The cross-couplings can provide powerful methods for the construction of biaryls and heterobiaryls; thus the development of a new coupling method has been intensively studied by synthetic chemists. Therefore, the oxidative biaryl coupling reaction of arenes containing a heteroatom is a significantly attractive, convenient, and straightforward route to the synthesis of biaryls due to its operational simplicity avoiding the preparation of the corresponding halogenated and metallated arenes. In this report, recent progress in the field of metal-free oxidative cross-coupling reactions of aromatic compounds using hypervalent iodine(III) reagents, is presented.1 Introduction2 Cyanation and Halogenation Reactions of Heteroaromatic Compounds3 Biaryl Coupling Reaction of Heteroaromatic Compounds3.1 Regioselective Coupling Reaction of Thiophenes3.2 Cross-Coupling Reaction of Thiophenes3.3 Coupling Reaction of EDOT and Pyrroles3.4 Cross-Coupling Reaction of Pyrroles4 Cross-Coupling Reaction of Anilines5 Cross-Coupling Reaction of Phenols6 Cross-Coupling Reaction of N-Heteroaromatics with Aryl Radicals from Diaryliodonium(III) Salts7 Conclusion

Potassium tert-Butoxide Mediated Reductive C–P Cross-Coupling of Arylvinyl Sulfides through C–S Bond Cleavage

Synlett ◽  
2020 ◽  
Author(s):  
Qingle Zeng ◽  
Jie Feng ◽  
Qiaoling Zhang ◽  
Fuhai Li ◽  
Lu Yang ◽  
...  
Keyword(s):  
Double Bond ◽  
Transition Metal ◽  
Bond Cleavage ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Phosphine Oxides ◽  
One Pot ◽  
Metal Free ◽  
Cross Coupling Reaction

AbstractA transition-metal-free t-BuOK-mediated reductive C–P cross-coupling reaction of arylvinyl sulfides with diarylphosphine oxides through C–S bond cleavage has been developed. This protocol not only permits the synthesis of diaryl(2-arylethyl)phosphine oxides, but also achieves an unprecedented construction of a C–P bond through C–S bond cleavage and reduction of a C–C double bond in one pot.

High-yielding sequential one-pot synthesis of chiral and achiral α-substituted acrylates via a metal-free reductive coupling reaction

2014 ◽  
Vol 12 (29) ◽  
pp. 5400-5406 ◽  
Author(s):  
Dhevalapally B. Ramachary ◽  
Chintalapudi Venkaiah ◽  
Y. Vijayendar Reddy
Keyword(s):  
Coupling Reaction ◽  
Reductive Coupling ◽  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Excellent Selectivity

A variety of chiral and achiral α-substituted acrylates were furnished in very good yields with excellent selectivity by using an organocatalytic reductive coupling reaction (TCRA) followed by an Eschenmoser methylenation.

Expedient and efficient one pot synthesis of trifluoroethyl ethers from metal free 2,4,6-tris-(2,2,2-trifluoro-ethoxy)-[1,3,5] triazene

RSC Advances ◽  
2015 ◽  
Vol 5 (44) ◽  
pp. 35042-35045 ◽  
Author(s):  
Shrawan Kumar Mangawa ◽  
Chiranjeev Sharma ◽  
Ashawani kumar Singh ◽  
Satish K. Awasthi
Keyword(s):  
Efficient Synthesis ◽  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Aryl Ethers

An efficient synthesis of fluorinated alkyl and aryl ethers was achieved by the use of s-triazene derived fluorinated reagent 2,4,6-tris-(2,2,2-trifluoro-ethoxy)-[1,3,5] triazene (TriTFET).

Sign in / Sign up

Export Citation Format

Share Document