85006-08-2Relevant academic research and scientific papers
Rhodium-Catalyzed Carbonylative Synthesis of Aryl Salicylates from Unactivated Phenols
Ai, Han-Jun,Zhang, Youcan,Zhao, Fengqian,Wu, Xiao-Feng
supporting information, p. 6050 - 6054 (2020/10/02)
A rhodium-catalyzed carbonylative transformation of unactivated phenols to aryl salicylates is described. This protocol is characterized by utilizing 1,3-rhodium migration as the key step to provide direct access to synthesize ohydroxyaryl esters. Various desired aryl o-hydroxybenzoates were produced in moderate to excellent yields with bis(dicyclohexylphosphino)ethane (DCPE) as the ligand. Interestingly, diphenyl carbonate was formed as the main product when 1,3-bis(diphenylphosphino)propane (DPPP) was used as the ligand. A plausible reaction mechanism is proposed.
Metal Template ortho-Acylation of Phenols. Direct Synthesis of Salicylic Acid Chlorides and Derivatives
Sartori, Giovanni,Casnati, Giuseppe,Bigi, Franca,Bonini, Giovanni
, p. 763 - 766 (2007/10/02)
A direct synthesis of salicylic acid chlorides is achieved via "metal-driven" intracomplex acylation of bromomagnesium and aluminum phenoxides with phosgene.Salicylic acids 5 and some derivatives 6, 7 can be obtained by quenching the reaction mixture with convenient reagents.Moreover the reaction of lithium phenylacetylide with 3 provides a new convenient approach to ortho-hydroxyaryl alkynyl ketones like 8.The oriented complex 2, involving the metal phenoxide and phosgene is proposed to account for the ortho-regioselective control of the reaction.
