142087-16-9Relevant academic research and scientific papers
Pseudocyclic Arylbenziodoxaboroles: Efficient Benzyne Precursors Triggered by Water at Room Temperature
Yoshimura, Akira,Fuchs, Jonathan M.,Middleton, Kyle R.,Maskaev, Andrey V.,Rohde, Gregory T.,Saito, Akio,Postnikov, Pavel S.,Yusubov, Mekhman S.,Nemykin, Victor N.,Zhdankin, Viktor V.
, p. 16738 - 16742 (2017)
New organohypervalent iodine compounds, arylbenziodoxaborole triflates, were prepared from 1-acetoxybenziodoxaboroles and arenes by treatment with trifluoromethanesulfonic acid under mild conditions. Single crystal X-ray crystallography of these compounds revealed a pseudocyclic structure with a short intramolecular interaction of 2.698 to 2.717 ? between oxygen and iodine in the benziodoxaborole ring. These new pseudocyclic aryliodonium salts readily generate aryne intermediates upon treatment with water at room temperature. The generated aryne intermediates react with various substrates to give the corresponding aryne adducts in moderate to good yields. Furthermore, the new benzyne precursors can also work as arylating reagents towards aromatic rings. The aryne intermediates generated from arylbenziodoxaborole triflates selectively react with tert-butyl phenol forming products of ortho arylation in moderate yields.
Facile one-pot synthesis of diarylacetylenes from arylaldehydes: Via an addition-double elimination process
Chen, Jianyang,Zhang, Xuan,Wu, Jiajun,Wang, Rui,Lei, Chunlin,An, Yanan
supporting information, p. 4701 - 4705 (2021/06/11)
A practical one-pot protocol has been developed to synthesize diarylacetylenes from arylaldehydes by treatment with 1-(arylmethyl)benzotriazoles and LiN(SiMe3)2. The reaction proceeded through imine formation, Mannich-type addition and double elimination to deliver products in up to 99% yields with broad substrate scope. In addition, gram-scale synthesis of 1-bromo-4-(phenylethynyl)benzene has been demonstrated.
Reactivity of AllylSmBr/HMPA: Facile Synthesis of 3-Aryl-1,2,4- benzotriazines
Yin, Ruifeng,Zhou, Liejin,Liu, Huili,Mao, Hui,Lue, Xin,Wang, Xiaoxia
, p. 143 - 148 (2013/08/24)
3-Aryl-1,2,4-benzotriazines were conveniently prepared in moderate to good yields from 1,l-bis(benzotriazol-1-yl)methylarenes with allylsamarium bromide/hexamethylphosphramide (allylSmBr/HMPA). Preliminary results indicate that HMPA may enhance the reduci
Convenient and stereoselective synthesis of symmetrical (E)-stilbenes via homocoupling of 1,3-dibenzylbenzotriazolium bromides
Xiao, Xiaohui,Lin, Daqin,Tong, Shuitian,Luo, Hong,He, Yinfeng,Mo, Hailan
supporting information; experimental part, p. 1731 - 1734 (2011/09/16)
Using NaH as the base and DMSO as the solvent, a series of symmetric (E)-stilbenes were prepared in good yields via the -homocoupling of 1,3-dibenzylbenzotriazolium bromides at room temperature. Georg Thieme Verlag Stuttgart · New York.
Construction of 3-aryl-1,2,4-benzotriazines via unprecedented rearrangement of bis(benzotriazol-1-yl)methylarenes
Zhong, Zhiyun,Hong, Ran,Wang, Xiaoxia
body text, p. 6763 - 6766 (2011/02/24)
3-Aryl-1,2,4-benzotriazines were formed unexpectedly by the treatment of 1,l-bis(benzotriazol-1-yl)methylarenes with allylsamarium bromide. A radical pathway was proposed involving steps, such as fragmentation, ring-opening, and cyclization.
Nucleophilic substitution of benzotriazolylalkyl chlorides with Grignard reagents: A direct route to benzotriazoloalkyl(hetero)aromatic compounds
Katritzky, Alan R.,Abdel-Fattah, Ashraf A. A.,Tymoshenko, Dmytro O.,Belyakov, Sergei A.
, p. 1437 - 1440 (2007/10/03)
Benzotriazolylalkyl chlorides 5 react with (hetero)aromatic Grignard reagents generated from the corresponding halogen derivatives to afford benzotriazoloalkyl(hetero)aromatic compounds 8a-k and 10a-c in good yields.
STUDIES ON THE THERMAL DECARBOXYLATION OF 1-ALKOXYCARBONYLBENZOTRIAZOLES
Katritzky, Alan R.,Zhang, Gui-Fen,Fan, Wei-Qiang,Wu, Jing,Pernak, Juliusz
, p. 567 - 573 (2007/10/02)
1-Alkoxycarbonylbenzotriazoles on thermolysis lose carbon dioxide; the decarboxylation is accompanied by the formation of a mixture of 1- and 2-alkylbenzotriazoles, with the N-1 isomer predominating over the N-2 isomer in all cases.A cross-over experiment
