89346-59-8Relevant academic research and scientific papers
Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes
He, Qing,Wang, Liwen,Liang, Yong,Zhang, Zunting,Wnuk, Stanislaw F.
, p. 9422 - 9427 (2016/10/17)
Transition-metal-free LiCl-promoted cross-coupling reactions of tetraphenyltin, trichlorophenyl-, dichlorodiphenyl-, and chlorotriphenylstannanes with aryl halides in DMF provided access to biaryls in good to high yields. Up to four phenyl groups were transferred from the organostannanes substrates. The aryls bearing electron-withdrawing groups in either halides or organotin substrates gave coupling products in higher yields. The methodology has been applied for the efficient synthesis of ipriflavones.
Strongly Directing Substituents in the Radical Arylation of Substituted Benzenes
Hofmann, Josefa,Clark, Timothy,Heinrich, Markus R.
, p. 9785 - 9791 (2016/10/31)
Although general interest in radical arylation reactions has grown rapidly in recent years, poor regioselectivities and the need to use a large excess of the radical-accepting arene have hindered their application to substituted benzenes. We now describe experimental and computational investigations into the substituent effects that lead to regioselective addition based on the recent discovery of anilines as outstanding substrates for radical arylations.
Phase-Transfer-Catalyzed Gomberg-Bachmann Synthesis of Unsymmetrical Biarenes: A Survey of Catalysts and Substrates
Beadle, James R.,Korzeniowsky, Stephen H.,Rosenberg, David E.,Garcia-Slanga, Blanche J.,Gokel, George W.
, p. 1594 - 1603 (2007/10/02)
Two problems have hindered the Gomberg-Bachmann (GB) and Pschorr reactions of arenediazonium cations: the instability of the arenediazonium salts and side reactions.Arenediazonium tetrafluoroborate and hexafluorophosphate salts can be prepared in high yield and purity and can be stored safely.Unfortunately, these salts are insoluble in most nonpolar organic solvents.Crown ether complexation or other phase-transfer (pt) catalytic methodology can ameliorate this situation, and reactions conducted by the approaches outlined herein often afforded coupling or cyclization products in high yield and corresponding purity.The use of crown ethers, quarternary 'onium salts, lipophilic carboxylic acid salts, and even the polar cosolvent acetonitrile increase the utility of the ptGB reaction dramatically.Sixty examples of couplings are reported along with an assessment of selectivities.A number of examples are also presented of phase-transfer-type Pschorr cyclizations.In the latter case, the use of potassium superoxide, KO2, is introduced to suppress indazole formation.
