18622-12-3Relevant academic research and scientific papers
Quantum Dot-Catalyzed Photoreductive Removal of Sulfonyl-Based Protecting Groups
Perez, Kaitlyn A.,Rogers, Cameron R.,Weiss, Emily A.
supporting information, p. 14091 - 14095 (2020/06/08)
This Communication describes the use of CuInS2/ZnS quantum dots (QDs) as photocatalysts for the reductive deprotection of aryl sulfonyl-protected phenols. For a series of aryl sulfonates with electron-withdrawing substituents, the rate of deprotection for the corresponding phenyl aryl sulfonates increases with decreasing electrochemical potential for the two electron transfers within the catalytic cycle. The rate of deprotection for a substrate that contains a carboxylic acid, a known QD-binding group, is accelerated by more than a factor of ten from that expected from the electrochemical potential for the transformation, a result that suggests that formation of metastable electron donor–acceptor complexes provides a significant kinetic advantage. This deprotection method does not perturb the common NHBoc or toluenesulfonyl protecting groups and, as demonstrated with an estrone substrate, does not perturb proximate ketones, which are generally vulnerable to many chemical reduction methods used for this class of reactions.
Formation of meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols from cyclohexane-1,3-diones
Do Van Thanh, Nhan,Patra, Subrata,Clive, Derrick L.J.
, p. 4343 - 4350 (2018/07/13)
Reaction of cyclohexane-1,3-diones with TsCl/Et3N and treatment of the resulting 3-(tosyloxy)cyclohex-2-en-1-ones with aryl- or alkyl thiols and K2CO3 in MeCN gives 3-(arylsulfanyl)cyclohex-2-en-1-ones or 3-(alkylsulfanyl)cyclohex-2-en-1-ones, respectively. These compounds are easily brominated at C-2 by using NBS in MeCN; exposure to DBU in MeCN at room temperature then causes aromatization to afford meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols.
Aryl/heteroaryl pentafluorobenzenesulfonates (ArOPFBs): New electrophilic coupling partners for room temperature Suzuki-Miyaura cross-coupling reactions
Joseph, Jayan T.,Sajith, Ayyiliath M.,Ningegowda, Revanna C.,Nagaraj, Archana,Rangappa,Shashikanth, Sheena
supporting information, p. 5106 - 5111 (2015/08/06)
The first cross-coupling reaction between aryl/heteroaryl pentafluorobenzenesulfonates and aryl/heteroaryl boronic acids under mild conditions is described. The successful synthesis of highly ortho substituted biaryls and high chemoselectivity of these bench stable intermediates over tosylates, triflates, mesylates, and chlorides increases its scope as a valuable cross-coupling partner. The generality of this protocol was further extended to other boron containing nucleophiles (boronates, trifluoroborates) and alkyl boronic acids.
