91639-72-4Relevant articles and documents
A Photosensitizer-Free Radical Cascade for Synthesizing CF3-Containing Polycyclic Quinazolinones with Visible Light
Hu, Qiang,Yu, Wan-Lei,Luo, Yong-Chun,Hu, Xiu-Qin,Xu, Peng-Fei
, p. 1493 - 1501 (2022/02/07)
Herein, we report an efficient photoinduced radical tandem trifluoromethylation/cyclization reaction of N-cyanamide alkenes for the synthesis of functionalized quinazolinones. Importantly, the reaction is carried out under mild conditions without any addi
Visible Light and Hydroxynaphthylbenzimidazoline Promoted Transition-Metal-Catalyst-Free Desulfonylation of N-Sulfonylamides and N-Sulfonylamines
Hasegawa, Eietsu,Nagakura, Yuto,Izumiya, Norihiro,Matsumoto, Keisuke,Tanaka, Tsukasa,Miura, Tomoaki,Ikoma, Tadaaki,Iwamoto, Hajime,Wakamatsu, Kan
supporting information, p. 10813 - 10825 (2018/07/30)
A visible light promoted process for desulfonylation of N-sulfonylamides and -amines has been developed, in which 1,3-dimethyl-2-hydroxynaphthylbenzimidazoline (HONap-BIH) serves as a light absorbing, electron and hydrogen atom donor, and a household white light-emitting diode serves as a light source. The process transforms various N-sulfonylamide and -amine substrates to desulfonylated products in moderate to excellent yields. The observation that the fluorescence of 1-methyl-2-naphthoxy anion is efficiently quenched by the substrates suggests that the mechanism for the photoinduced desulfonylation reaction begins with photoexcitation of the naphthoxide chromophore in HONap-BIH, which generates an excited species via intramolecular proton transfer between the HONap and BIH moieties. This process triggers single electron transfer to the substrate, which promotes loss of the sulfonyl group to form the free amide or amine. The results of studies employing radical probe substrates as well as DFT calculations suggest that selective nitrogen-sulfur bond cleavage of the substrate radical anion generates either a pair of an amide or amine anion and a sulfonyl radical or that of an amidyl or aminyl radical and sulfinate anion, depending on the nature of the N-substituent on the substrate. An intermolecular version of this protocol, in which 1-methyl-2-naphthol and 1,3-dimethyl-2-phenylbenzimidazoline are used concomitantly, was also examined.
Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides
Rossi, Steven A.,Shimkin, Kirk W.,Xu, Qun,Mori-Quiroz, Luis M.,Watson, Donald A.
supporting information, p. 2314 - 2317 (2013/06/05)
For the first time, a general catalytic procedure for the cross-coupling of primary amides and alkylboronic acids is demonstrated. The key to the success of this reaction was the identification of a mild base (NaOSiMe3) and oxidant (di-tert-butyl peroxide) to promote the copper-catalyzed reaction in high yield. This transformation provides a facile, high-yielding method for the monoalkylation of amides.