106510-95-6Relevant academic research and scientific papers
Relative Reactivities of Hetaryl Radicals in Hydrogen Atom Abstraction and Nucleophilic Addition Ractions
Zoltewicz, John A.,Locko, George A.
, p. 4214 - 4219 (1983)
The 3-pyridyl, 4-isoquinolyl and 3-quinolyl ? radicals were generated photochemically from their corresponding halides in the presence of sodium methoxide and thiophenoxide in methanol.Each radical in competition abstracts a hydrogen atom from either methoxide ion or methanol or adds thiophenoxide ion.The corresponding reduction to substitution product ratios give rate constant ratios which are similar for the three hetaryl radicals, showing only a small influence of radical structure on relative reactivity.The thiolate ion is 2-5 times more reactive than methoxide ion; methoxide on the average is 39 times more reactive than methanol.
Nature of the Reactions Involving 4-Haloisoquinolines and Amide Ion in Ammonia. Remarkable Competition between SRN1 Substitution and ? Complex Formation
Zoltewicz, John A.,Oestreich, Terence M.
, p. 2805 - 2809 (1991)
4-Bromo- (1) or 4-chloroisoquinoline (3) in refluxing liquid ammonia containing amide and thiomethoxide reacts preferentially with the thiolate ion to give 4-(methylthio)isoquinoline (2) in high yield.The bromo substrate was shown to require amide ion in order to react with thiomethoxide ion, no reaction taking place in its absence.Substitution product is believed to form from both halides by an SRN1 mechanism.By contrast, 3-chloroisoquinoline under the same conditions of mixed anions gives 3-aminoisoquinoline.The role of amide ion and its addition to give ? complexes in these and other reactions of 4-halogenated isoquinolines in ammonia is discussed.
Visible-Light-Driven Halogen-Bond-Assisted Direct Synthesis of Heteroaryl Thioethers Using Transition-Metal-Free One-Pot C-I Bond Formation/C-S Cross-Coupling Reaction
Nandy, Anuradha,Kazi, Imran,Guha, Somraj,Sekar, Govindasamy
, p. 2570 - 2581 (2021/02/27)
An efficient protocol for the synthesis of thioether directly from heteroarenes has been developed in the presence of visible light in a one-pot manner at room temperature. This method involves two sequential reactions in a single pot where the formation of the iodinated heteroarene is followed by a transition-metal-free C-S coupling reaction. A wide range of heteroarene and thiol partners (including aliphatic thiols) have been used for the synthesis of thioethers. NMR studies and DFT calculations revealed the presence of a halogen bond between the thiolate anion (halogen bond acceptor) and iodoheteroarene (halogen bond donor). This halogen bonded complex on photoexcitation facilitates the electron transfer from the thiolate anion to the iodoheteroarene at room temperature.
A highly efficient heterogeneous copper-catalyzed Chan-Lam coupling between thiols and arylboronic acids leading to diaryl sulfides under mild conditions
Lin, Yang,Cai, Mingzhong,Fang, Zhiqiang,Zhao, Hong
, p. 3335 - 3343 (2016/05/19)
The heterogeneous Chan-Lam coupling reaction between thiols and arylboronic acids was achieved in EtOH at room temperature in the presence of 5 mol % of MCM-41-immobilized 1,10-phenanthroline-copper(II) complex [MCM-41-1,10-Phen-CuSO4] with n-Bu4NOH (40% aq) as base under O2 atmosphere, yielding a variety of unsymmetrical diaryl sulfides in good to excellent yields under mild and green conditions. The new heterogeneous copper complex can easily be prepared by a simple procedure from commercially readily available and inexpensive reagents, and recovered by a simple filtration of the reaction solution and recycled for at least eight times without significant loss of catalytic activity.
