250660-51-6Relevant articles and documents
One pot tandem dual CC and CO bond reductions in the β-alkylation of secondary alcohols with primary alcohols by ruthenium complexes of amido and picolyl functionalized N-heterocyclic carbenes
Dey, Shreyata,Ghosh, Prasenjit,Prakasham, A. P.,Ta, Sabyasachi
, p. 15640 - 15654 (2021/11/30)
Two different classes of ruthenium complexes, namely, [1-mesityl-3-(2,6-Me2-phenylacetamido)-imidazol-2-ylidene]Ru(p-cymene)Cl (1c) and {[1-(pyridin-2-ylmethyl)-3-(2,6-Me2-phenyl)-imidazol-2-ylidene]Ru(p-cymene)Cl}Cl (2c), successfully catalyzed the one-pot tandem alcohol-alcohol coupling reactions of a variety of secondary and primary alcohols, in moderate to good yields of ca. 63-89%. The mechanistic investigation performed on two representative catalytic substrates, 1-phenylethanol and benzyl alcohol using the neutral ruthenium (1c) complex showed that the catalysis proceeded via a partially reduced CC hydrogenated carbonyl species, [PhCOCH2CH2Ph] (3′), to the fully reduced CO and CC hydrogenated secondary alcohol, [PhCH(OH)CH2CH2Ph] (3). Furthermore, the time dependent study showed that the major product of the catalysis modulated between (3′) and (3) during the catalysis run performed over an extended period of 120 hours. Finally, the practical utility of the alcohol-alcohol coupling reaction was demonstrated by preparing five different flavan derivatives (13-17) related to various bioactive flavonoid natural products, in a one-pot tandem fashion.
A Modular Synthesis of 2-Alkyl- and 2-Arylchromans via a Three-Step Sequence
Orr, Robert K.,Campeau, Louis-Charles,Chobanian, Harry R.,McCabe Dunn, Jamie M.,Pio, Barbara,Plummer, Christopher W.,Nolting, Andrew,Ruck, Rebecca T.
, p. 657 - 666 (2017/01/28)
A convergent three-step method for the synthesis of 2-substituted chromans is described. These results have been accomplished via the Heck coupling of readily accessible allylic alcohols and 2-iodophenols, followed by reduction and Mitsunobu cyclization. The utility and generality of this method is demonstrated through the synthesis of a series of 2-aryl-, 2-heteroaryl- and 2-alkylchromans, as well as an azachroman derivative. The asymmetric version of this approach via a Noyori-catalyzed ketone reduction and subsequent cyclization is likewise highlighted.
Transition metals catalyzed C-C and C-O bonds formation: Facile synthesis of flavans and benzoxepines
Ramulu, B. Venkat,Mahendar,Krishna,Reddy, A. Gopi Krishna,Suchand,Satyanarayana
, p. 8305 - 8315 (2013/09/02)
A simple and practical method has been developed based on intermolecular [Pd]-catalyzed C-C and an intramolecular [Cu]-catalyzed C-O bond formations for the synthesis of flavans and benzoxepines. Interestingly, the method is amenable for the synthesis of