154274-94-9Relevant articles and documents
Transition metal-free protodecarboxylation of electron rich aromatic acids under mild conditions
Fang, Jingxian,Wang, Dangui,Deng, Guo-Jun,Gong, Hang
supporting information, p. 4503 - 4506 (2017/10/30)
A mild and practical method for the transition metal-free protodecarboxylation of aromatic acids using readily available and safe sodium persulfate as initiator was described. This environment-friendly decarboxylation approach was performed at 60 °C in ethanol and could easily scale up to the gram level with a good yield. In Particular, the tandem reactions of decarboxylation and halogenation were achieved by the addition of the corresponding halogenating reagents to the reaction system.
Exploring the Reactivity of α-Lithiated Aryl Benzyl Ethers: Inhibition of the [1,2]-Wittig Rearrangement and the Mechanistic Proposal Revisited
Velasco, Rocío,Silva López, Carlos,Nieto Faza, Olalla,Sanz, Roberto
supporting information, p. 15058 - 15068 (2016/10/11)
By carefully controlling the reaction temperature, treatment of aryl benzyl ethers with tBuLi selectively leads to α-lithiation, generating stable organolithiums that can be directly trapped with a variety of selected electrophiles, before they can undergo the expected [1,2]-Wittig rearrangement. This rearrangement has been deeply studied, both experimentally and computationally, with aryl α-lithiated benzyl ethers bearing different substituents at the aryl ring. The obtained results support the competence of a concerted anionic intramolecular addition/elimination sequence and a radical dissociation/recombination sequence for explaining the tendency of migration for aryl groups. The more favored rearrangements are found for substrates with electron-poor aryl groups that favor the anionic pathway.
Gold-catalyzed ethynylation of arenes
De Haro, Teresa,Nevado, Cristina
supporting information; experimental part, p. 1512 - 1513 (2010/04/04)
(Figure Presented) A novel gold-catalyzed ethynylation of aromatic rings with electron-deficient alkynes via gold catalyzed C-H activation of both C sp-H and Csp2-H bonds has been developed. This transformation provides aromatic propiolates difficult to prepare by other methods, highlighting the synthetic potential of gold chemistry.
