58468-99-8Relevant articles and documents
Boron Lewis Acid-Catalyzed Regioselective Hydrothiolation of Conjugated Dienes with Thiols
Kumar, Gautam,Qu, Zheng-Wang,Ghosh, Soumen,Grimme, Stefan,Chatterjee, Indranil
, p. 11627 - 11633 (2019/12/02)
A transition-metal-free hydrothiolation of 1,3-dienes for the synthesis of secondary and tertiary allylic sulfides is reported. The boron Lewis acids tris(pentafluorophenyl)borane, B(C6F5)3, and BF3·Et2O are shown to catalyze the regioselective hydrothiolation of a wide range of terminal 1-aryl-1,3-dienes. In the case of internal 1,3-dienes, B(C6F5)3 is by far the better catalyst than BF3·Et2O. The process features mild reaction conditions, broad scope, and low catalyst loading, and it can be scaled up quickly over a short reaction time. The reactions are rate-limited by the 1-aryl-directed protonation of 1,3-dienes with thiol-boron Lewis acid complexes, followed by sulfide anion transfer to the resultant allyl cations, as revealed by high-level DFT calculations.
FACILE FUNCTIONALIZATION OF THE ISOPROPYLIDENE TERMINUS OF ACYCLIC MONOTERPENES BY WAY OF BENZENESULFENYL CHLORIDE ADDITION
Masaki, Yukio,Hashimoto, Kinji,Kaji, Kenji
, p. 3481 - 3490 (2007/10/02)
Highly site- and regioselective terminal functionalizations of acyclic monoterpenes 1 via benzenesulfenyl chloride addition followed by hydrolysis assisted by silica gel, dehydrochlorination under neutral or weakly basic condition, or dehydrochlorination by strongly basic treatment respectively providing β-hydroxy sulfides 3, terminal methallylic sulfides 4, or vinylsulfides 5 are developed.Conversion of 4 to terminal trans-allylic alcohols 10 via sulfoxides 9 by the Evans procedure is also described.
