7294-69-1

Upstream product

• 7294-51-1 2,4,6-tris(4-methoxyphenyl)boroxine 
• 10294-34-5 boron trichloride 
• 21502-70-5 tris(p-anisyl)antimony 
• 2097-72-5 bis(p-anisyl)mercury 

Downstream Products

• 5720-07-0 4-methoxyphenylboronic acid 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 1739-27-1 (4-CH₃OC₆H₄)BClN(C₂H₅)2 
• 40927-73-9 4-CH₃OC₆H₄BClN(CH₃)(CH₂C₆H₅) 
• 19127-89-0 4-CH₃O-C₆H₄B{N(CH₃)2}2 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 27331-33-5 1-(4-methoxyphenyl)naphthalene 
• 611-94-9 4-Methoxybenzophenone 
• 99980-57-1 (n-C₄H₉O)BClC₆H₄-4-OCH₃ 
• 34907-51-2 4-CH₃OC₆H₄B(O-n-C₄H₉)2 

Relevant academic research and scientific papers

Synthesis of arylboronates by boron-induced ipso-deantimonation of triarylstibanes with boron trihalides and its application in one-pot two-step transmetallation/cross-coupling reactions

The reaction of triarylstibanes (1) with boron trihalides (BCl3, and BBr3) afforded arylboron dihalides (2) by utilizing all the three aryl groups on the antimony. Boron intermediates (2) were transformed to arylboronates (3) in good to excellent yields by treatment with methanol and 1,3-propanediol. Further, the Pd-catalyzed reactions of 2 with organic halides such as 1-bromonaphthalene and benzoyl chloride in the presence of H2O afforded the corresponding cross-coupling products, unsymmetrical biaryls (4) and ketones (5), in moderate to good yields. The potential energy surfaces for the transmetallations of triarylstibanes (1) with BCl3 affording 2 were determined by molecular orbital calculations. The analyses of substituent effects on theoretically calculated reactivities showed the importance of the resonance effects of the ring substituents on these transmetallations.