A direct route from white phosphorus and fluorous alkyl and aryl iodides to the corresponding trialkyl- and triarylphosphines

2018 ◽  
Vol 5 (23) ◽  
pp. 3421-3429 ◽  
Author(s):  
Subrata K. Ghosh ◽  
Christopher C. Cummins ◽  
John A. Gladysz
Keyword(s):  
Bond Cleavage ◽  
White Phosphorus ◽  
Title Reaction ◽  
Direct Route ◽  
Aryl Iodides

The title reaction is effected with samarium(ii) reductants that generate fluorous radicals that add to P4 with phosphorus–phosphorus bond cleavage.

Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides

Synlett ◽  
2022 ◽  
Author(s):  
Fan Wu ◽  
Wei Wang ◽  
Ken Yao
Keyword(s):  
Electron Transfer ◽  
Transfer Process ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
Direct Access ◽  
Single Electron Transfer ◽  
Mechanistic Studies ◽  
Electron Transfer Process ◽  
Sulfonium Salts ◽  
Aryl Iodides

A nickel-catalyzed cross-electrophile coupling of benzylic sulfonium salts with aryl iodides has been developed, providing direct access to diarylalkanes from readily available and stable coupling partners. Preliminary mechanistic studies suggest that the C–S bond cleavage proceeds through a single-electron transfer process to generate a benzylic radical.

Metal-free n-Et4NBr-catalyzed radical cyclization of disulfides and alkynes leading to benzothiophenes under mild conditions

RSC Advances ◽  
2014 ◽  
Vol 4 (89) ◽  
pp. 48547-48553 ◽  
Author(s):  
Daoshan Yang ◽  
Kelu Yan ◽  
Wei Wei ◽  
Laijin Tian ◽  
Qinghe Li ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Bond Formation ◽  
Environmentally Friendly ◽  
Radical Cyclization ◽  
Title Reaction ◽  
Metal Free ◽  
Mild Conditions

The title reaction involves metal free TEAB-catalyzed S–S bond cleavage, C–S bond formation and C–C bond formation; it uses readily available disulfides and alkynes as substrates, and environmentally friendly TEAB as catalyst to synthesize useful benzothiophene derivatives.

scholarly journals Nickel-catalyzed carbonylation of thioacetates with aryl iodides via CO insertion and C–S bond cleavage

2021 ◽  
pp. 174751982110281
Author(s):  
Wen-Peng Mai ◽  
Hong-Da Sui ◽  
Ming-Xiu Lv ◽  
Kui Lu
Keyword(s):  
Carbon Monoxide ◽  
Bond Cleavage ◽  
Cost Effective ◽  
Direct Approach ◽  
Coupling Process ◽  
Aryl Iodides ◽  
Co Insertion

Aryl thioesters are synthesized via nickel-catalyzed carbonylation of thioacetates with aryl iodides. Alkyl thioacetates undergo coupling with carbon monoxide and aryl iodides to produce the desired aryl thioesters in moderate yields. This catalytic carbonylative coupling process provides a cost-effective and direct approach for the preparation of useful thioesters.

A practical ortho-acylation of aryl iodides enabled by moisture-insensitive activated esters via palladium/norbornene catalysis

2020 ◽  
Vol 7 (21) ◽  
pp. 3420-3426
Author(s):  
Yunxia Feng ◽  
Yangyang Wang ◽  
Shen Zhao ◽  
Dao-Peng Zhang ◽  
Xinjin Li ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Activated Esters ◽  
Aryl Iodides

Herein reported is a practical Catellani-type ortho-acylation of aryl iodides enabled by employing moisture-insensitive esters as the electrophile via C(O)–O bond cleavage.

Selective heterolytic P–P bond cleavage of white phosphorus by a frustrated carbene-borane Lewis pair

2010 ◽  
Vol 39 (44) ◽  
pp. 10590 ◽  
Author(s):  
Dirk Holschumacher ◽  
Thomas Bannenberg ◽  
Kerstin Ibrom ◽  
Constantin G. Daniliuc ◽  
Peter G. Jones ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
White Phosphorus

Synthesis of S-aryl thioesters via palladium-catalyzed thiocarbonylation of aryl iodides and aryl sulfonyl hydrazides

2020 ◽  
Vol 7 (19) ◽  
pp. 2938-2943
Author(s):  
Yeojin Kim ◽  
Kwang Ho Song ◽  
Sunwoo Lee
Keyword(s):  
Aryl Iodide ◽  
Aryl Iodides ◽  
Palladium Catalyzed

Aryl sulfonyl hydrazide reacted with aryl iodide in the presence of CO to give the corresponding S-aryl thioesters.

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