16407-55-9Relevant articles and documents
Intercepting the Breslow intermediate via Claisen rearrangement: Synthesis of complex tertiary alcohols without organometallic reagents
Alwarsh, Sefat,Ayinuola, Kolawole,Dormi, Silvana S.,McIntosh, Matthias C.
supporting information, p. 3 - 5 (2013/03/28)
A novel Claisen rearrangement in which the Breslow intermediate is engaged as a hydroxy-substituted N,S-ketene acetal to provide complex 3° alcohols without the use of organometallic reagents is reported. The reaction constitutes an unprecedented reactivi
Pd(ii) complexes of N,S-heterocyclic carbenes with pendant and coordinated allyl function and their Suzuki coupling activities
Yen, Swee Kuan,Koh, Lip Lin,Huynh, Han Vinh,Hor, T. S. Andy
, p. 3952 - 3958 (2008/02/12)
3-(2-Propenyl)benzothiazolium bromide (A) provides a direct and simple entry to Pd(ii) complexes with N,S-heterocyclic carbene (NSHC) ligands functionalized with an allyl pendant with hemilabile potential. Addition of salt A to Pd(OAc)2 eliminates HOAc and affords the bis(carbene) complexes cis-[PdBr2(NHSC)2] (cis-1, NSHC = 3-(2-propenyl) benzothiazolin-2-ylidene) and trans-[PdBr2(NHSC)2] (trans-1) along with the monocarbene complexes [PdBr2(NSHC)] (2) and trans-[PdBr2(benzothiazole-κN)(NSHC)] (3) as minor side products. Salt-metathesis of cis-1 with AgO2CCF3 yields the mixed dicarboxylato-bis(carbene) complex cis-[Pd(O2CCF 3)2(NSHC)2] (4). Complexes cis-1, trans-1 and 4 were characterized by multinuclear NMR spectroscopies, ESI mass spectrometry and elemental analysis. The molecular structures of complexes cis-1, 2 and 3 have been determined by X-ray single crystal diffraction. Complexes cis-1 and 4 as well as an in situ mixture of Pd(OAc)2 and salt A are active toward Suzuki-Miyaura coupling of aryl bromides and activated aryl chlorides giving good conversions. The Royal Society of Chemistry.