142075-25-0Relevant academic research and scientific papers
Tert-Butyl Sulfoxides: Key Precursors for Palladium-Catalyzed Arylation of Sulfenate Salts
Gelat, Fabien,Lohier, Jean-Fran?ois,Gaumont, Annie-Claude,Perrio, Stéphane
supporting information, p. 2011 - 2016 (2015/06/23)
The present report describes an efficient and clean generation of sulfenate salts (R1SO-) by pyrolysis of readily available tert-butyl sulfoxides to give sulfenic acids (R1SOH) and traceless isobutene, followed by hydrogen abstraction with a weak inorganic base (K3PO4). The relevance of this process was exemplified through an in situ palladium-catalyzed cross-coupling reaction with aryl halides/triflates leading to aryl sulfoxides. The operationally simple C-S bond-forming protocol developed uses Pd(dba)2 as catalyst and Xantphos as ligand in toluene or a toluene/H2O mixture. Further extensions include the use of di-tert-butyl sulfoxide as an equivalent for sulfur monoxide dianion (SO2-) and the development of diastereoselective versions in the [2.2]paracyclophane and biaryl series.
Diastereoconvergent synthesis of trans -5-hydroxy-6-substituted-2- piperidinones by addition-cyclization-deprotection process
Si, Chang-Mei,Huang, Wei,Du, Zhen-Ting,Wei, Bang-Guo,Lin, Guo-Qiang
supporting information, p. 4328 - 4331 (2014/09/30)
A diastereoselective one-pot approach to access trans-5-hydroxy-6- substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by α-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.
The tert-butyl sulfoxide directed ortho metalation group. New synthetic methodology for substituted aromatics and pyridines and comparison with other metalation directors
Quesnelle,Iihama,Aubert,Perrier,Snieckus
, p. 2625 - 2628 (2007/10/02)
Details of the directed ortho metalation of tert-butyl phenyl sulfoxide (1) and 2- and 4-tert-butyl pyridyl sulfoxides (3a,b) are described along with comparisons with established metalation directors (CONR2, OCONR2, OMOM, SO2t-Bu) via inter- and intramolecular competition experiments.
