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Upstream product

• 75877-33-7 C₅H₅BCl₂S 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 554-14-3 2-Methylthiophene 
• 5419-55-6 Triisopropyl borate 
• 162607-20-7 (5-methylthiophen-2-yl)boronic acid 
• 72835-25-7 2-cyano-5-methylthiophene 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 

Relevant academic research and scientific papers

Synthesis of sexithiophene-bridged cage compound: A new class of three-dimensionally expanded oligothiophenes

A bicyclo-type cage-shaped compound consisting of three sexithiophenes was successfully synthesized and characterized by NMR, HRMS, and X-ray crystallographic analysis. The strained cage architecture was reflected in the blue-shifted absorption spectrum relative to its linear analogue. Intramolecular interaction between three-dimensionally fixed sexithiophenes was suggested by electrochemical analysis.

Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C-O Arylation of Dimethoxyanthraquinones

A convenient method for the syntheses of dibenzo[h,rst]pentaphenes and dibenzo[fg,qr]pentacenes via the ruthenium-catalyzed chemoselective C-O arylation of 1,4- and 1,5-dimethoxyanthraquinones is described. Dimethoxyanthraquinones reacted selectively with

Fine-tuning the nucleophilic reactivities of boron ate complexes derived from aryl and heteroaryl boronic esters

Boron ate complexes derived from thienyl and furyl boronic esters and aryllithium compounds have been isolated and characterized by X-ray crystallography. Products and mechanisms of their reactions with carbenium and iminium ions have been analyzed. Kinet

Mechanistic studies into amine-mediated electrophilic arene borylation and its application in MIDA boronate synthesis

Direct electrophilic borylation using Y2BCl (Y2 = Cl2 or o-catecholato) with equimolar AlCl3 and a tertiary amine has been applied to a wide range of arenes and heteroarenes. In situ functionalization of the ArBCl2 products is possible with TMS 2MIDA, to afford bench-stable and easily isolable MIDA-boronates in moderate to good yields. According to a combined experimental and computational study, the borylation of activated arenes at 20 C proceeds through an S EAr mechanism with borenium cations, [Y2B(amine)] +, the key electrophiles. For catecholato-borocations, two amine dependent reaction pathways were identified: (i) With [CatB(NEt 3)]+, an additional base is necessary to accomplish rapid borylation by deprotonation of the borylated arenium cation (σ complex), which otherwise would rather decompose to the starting materials than liberate the free amine to effect deprotonation. Apart from amines, the additional base may also be the arene itself when it is sufficiently basic (e.g., N-Me-indole). (ii) When the amine component of the borocation is less nucleophilic (e.g., 2,6-lutidine), no additional base is required due to more facile amine dissociation from the boron center in the borylated arenium cation intermediate. Borenium cations do not borylate poorly activated arenes (e.g., toluene) even at high temperatures; instead, the key electrophile in this case involves the product from interaction of AlCl3 with Y2BCl. When an extremely bulky amine is used, borylation again does not proceed via a borenium cation; instead, a number of mechanisms are feasible including via a boron electrophile generated by coordination of AlCl3 to Y2BCl, or by initial (heteroarene)AlCl3 adduct formation followed by deprotonation and transmetalation.

Rhodium(I)-catalyzed borylation of nitriles through the cleavage of carbon-cyano bonds

The reaction of aryl cyanides with diboron in the presence of a rhodium/Xantphos catalyst and DABCO affords arylboronic esters via carbon-cyano bond cleavage. This unprecedented mode of reactivity for a borylrhodium species allows the regioselective intro