51942-32-6Relevant articles and documents
Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer
Xu, Ze-Ming,Li, Hong-Xi,Young, David James,Zhu, Da-Liang,Li, Hai-Yan,Lang, Jian-Ping
supporting information, p. 237 - 241 (2019/01/10)
Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.
Diverse Visible-Light-Promoted Functionalizations of Benzotriazoles Inspired by Mechanism-Based Luminescence Screening
Teders, Michael,Gómez-Suárez, Adrián,Pitzer, Lena,Hopkinson, Matthew N.,Glorius, Frank
supporting information, p. 902 - 906 (2017/01/13)
Three new visible-light-promoted functionalizations of benzotriazole substrates were discovered using a mechanism-based screening method. ortho-Thiolated, borylated, and alkylated N-arylbenzamide products were obtained under mild reaction conditions in a new denitrogenative synthetic approach to functionalized aniline derivatives. The functional group tolerance of the borylation reaction was further analyzed in the first application of an additive-based robustness screen in a photocatalytic transformation. All the functionalizations proceed via photocatalytically initiated chain mechanisms as indicated by determination of the reaction quantum yields and Stern–Volmer analyses.
Eliminative Ring Fission of 4-Acyl-2,3-dihydro-4H-1,4-benzothiazines
Babudri, F.,Florio, S.,Indelicati, G.,Trapani, G.
, p. 4082 - 4087 (2007/10/02)
The behavior of 4-acyl-2,3-dihydro-1,4-benzothiazines 1-11 upon treatment with lithium diisopropylamide (LDA) in THF at -78 deg C has been examined.Very marked differences have been observed.Whereas unsubstituted and monosubstituted derivatives (1-4) read