13319-71-6Relevant articles and documents
Aryne 1,2,3,5-Tetrasubstitution Enabled by 3-Silylaryne and Allyl Sulfoxide via an Aromatic 1,3-Silyl Migration
Shi, Jiarong,Li, Lianggui,Shan, Chunhui,Wang, Junli,Chen, Zhonghong,Gu, Rongrong,He, Jia,Tan, Min,Lan, Yu,Li, Yang
supporting information, p. 2178 - 2184 (2021/02/16)
Although benzyne has been well-known to serve as a synthon that can conveniently prepare various 1,2-difunctionalized benzenes, the sites other than its formal triple bond remain silent in typical benzyne transformations. An unprecedented aryne 1,2,3,5-tetrasubstitution was realized from 3-silylbenzyne and aryl allyl sulfoxide, the mechanistic pathway of which includes a regioselective aryne insertion into the SO bond, a [3,6]-sigmatropic rearrangement, and a thermal aromatic 1,3-silyl migration cascade.
Chiral Phosphine–Phosphite Ligands in Asymmetric Gold Catalysis: Highly Enantioselective Synthesis of Furo[3,4-d]-Tetrahydropyridazine Derivatives through [3+3]-Cycloaddition
Du, Qingwei,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther
supporting information, p. 2379 - 2383 (2018/01/27)
The AuI-catalyzed reaction of 2-(1-alkynyl)-2-alken-1-ones with azomethine imines regio- and diastereoselectively affords furo[3,4-d]tetrahydropyridazines in a tandem cyclization/intermolecular [3+3]-cycloaddition process under mild conditions.
Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide
Bovonsombat, Pakorn,Teecomegaet, Pattaradra,Kulvaranon, Panisanun,Pandey, Aditi,Chobtumskul, Kittithorn,Tungsirisurp, Sireethorn,Sophanpanichkul, Punyanuch,Losuwanakul, Satreerat,Soimaneewan, Dechathon,Kanjanwongpaisan, Patcharida,Siricharoensang, Pornpawit,Choosakoonkriang, Sirirat
, p. 6564 - 6572 (2017/10/17)
Regioselective monobromination of various aromatics was achieved at room temperature using N-bromosuccinimide and 5 mol% of thioamides in acetonitrile. With thiourea as catalyst, activated aromatics, such as anisole, acetanilide, benzamide and phenol analogues containing electron donating or withdrawing groups, were brominated with high regioselectivity. Room temperature brominations of weakly activated aromatics and deactivated 9-fluorenone were accomplished by 5 mol% thioacetamide, higher substrates concentrations and longer reaction times. A backbonding of the bromine lone pairs with the π*of C[dbnd]S group and a halogen bond between the halogen bond donor bromine and the halogen bond acceptor sulfur of the thioamide are thought to be the principal interactions and cause of N-bromosuccinimide activation.