6734-91-4

Usage

InChI:InChI=1/C14H14O/c1-2-15-14-11-7-6-10-13(14)12-8-4-3-5-9-12/h3-11H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 144190-64-7 bis(2,2'-biphenylylene)sulfurane 
• 19615-37-3 bis(2,2'-bisphenylylene)selenurane 
• 108-86-1 bromobenzene 
• 103-73-1 Phenetole 

Downstream Products

• 827-52-1 1-phenyl-1-cyclohexane 
• 92-52-4 biphenyl 
• 92-51-3 cyclohexylcyclohexane 
• 530084-81-2 6-ethoxy-biphenyl-3-ylamine 

Relevant academic research and scientific papers

The site-selectivity and mechanism of Pd-catalyzed C(sp2)-H arylation of simple arenes

Control over site-selectivity is a critical challenge for practical application of catalytic C-H functionalization reactions in organic synthesis. Despite the seminal breakthrough of the Pd-catalyzed C(sp2)-H arylation of simple arenes via a concerted metalation-deprotonation (CMD) pathway in 2006, understanding the site-selectivity of the reaction still remains elusive. Here, we have comprehensively investigated the scope, site-selectivity, and mechanism of the Pd-catalyzed direct C-H arylation reaction of simple arenes. Counterintuitively, electron-rich arenes preferably undergo meta-arylation without the need for a specifically designed directing group, whereas electron-deficient arenes bearing fluoro or cyano groups exhibit high ortho-selectivity and electron-deficient arenes bearing bulky electron-withdrawing groups favor the meta-product. Comprehensive mechanistic investigations through a combination of kinetic measurements and stoichiometric experiments using arylpalladium complexes have revealed that the Pd-based catalytic system works via a cooperative bimetallic mechanism, not the originally proposed monometallic CMD mechanism, regardless of the presence of a strongly coordinating L-type ligand. Notably, the transmetalation step, which is influenced by a potassium cation, is suggested as the selectivity-determining step.

Reactions of Selenurane with Alcohols, Thiols and Selenol. A Quest for Formation of a New ?-Selenurane , or

Bis(2,2'-biphenylylene)selenurane readily reacts with various alcohols, phenols, thiols and selenol to give ligand coupling or ipso-substitution products under mild conditions via a two-step mechanism involving a ?-selenurane , and or corresponding selenonium salts as intermediates.

REACTIONS AND MECHANISM OF BIS(2,2'-BIPHENYLYLENE)-SULFURANE WITH THE REAGENTS HAVING HYDROXYL GROUP.

Bis(2,2'-biphenylylene)sulfurane reacts readily with various alcohols, phenols, and thiols to give ligand coupling or ipso-substitution products under mild cocnditions via a two-step mechanism involving a ?-sulfuranes or corresponding sulfonium salts as intermediates.