6052-64-8Relevant academic research and scientific papers
Zinc-mediated α-regioselective Barbier-type cinnamylation reactions of aldehydes, ketones and esters
Zhao, Li-Ming,Gao, Hua-Shuai,Li, De-Feng,Dong, Jing,Sang, Lan-Lin,Ji, Jie
, p. 4359 - 4366 (2017/07/10)
We report a simple, efficient, and general method for the zinc-mediated regioselective cinnamylation of aldehydes and ketones under Barbier-type conditions in a one-pot synthesis affording the corresponding α-cinnamylated alcohols in moderate to excellent yields. Compared to the literature procedures, this approach is operationally simple, uses simple reactants, and provides direct access to linear α-cinnamylated alcohols with excellent regioselectivity. Experimental results suggest that the reactions proceed through the radical pathway. In addition, the reaction was found to be scalable to the gram-scale and the one-pot protocol is also applicable to less reactive esters leading to bishomoallylic alcohols which were valuable intermediates for desymmetrizing intramolecular Heck cyclization, allowing for the elaboration to functionalized building blocks.
Highly α-regioselective neodymium-mediated allylation of diaryl ketones
Zhang, Fang,Wang, Ru,Wu, San,Wang, Peipei,Zhang, Songlin
, p. 87710 - 87718 (2016/09/23)
The first utility of neodymium as a mediating-metal in the highly α-regioselective Barbier reaction of diaryl ketones with allyl halides is reported in this paper. This reaction was conveniently carried out under mild conditions in a one-pot fashion with
α-Regioselective Barbier Reaction of Carbonyl Compounds and Allyl Halides Mediated by Praseodymium
Wu, San,Li, Ying,Zhang, Songlin
, p. 8070 - 8076 (2016/09/09)
The first utility of praseodymium as a mediating metal in the Barbier reaction of carbonyl compounds with allyl halides was reported in this paper. In contrast to the traditional metal-mediated or catalyzed Barbier reactions, exclusive α-adducts were obta
Pd-catalyzed nucleophilic allylic alkylation of aliphatic aldehydes by the use of allyl alcohols
Kimura, Masanari,Shimizu, Masamichi,Tanaka, Shuji,Tamaru, Yoshinao
, p. 3709 - 3718 (2007/10/03)
Under catalysis of Pd(OAc)2-(P-n-Bu)3, Et 2Zn promotes a variety of allyl alcohols to undergo nucleophilic allylation of aliphatic aldehydes and ketones at room temperature and provides homoallyl alcohols in 60-90 and ca. 60% isolated yield, respectively. The reaction is irreversible and kinetically controlled, and unique regio- and stereoselectivities observed for the allylation with unsymmetrically substituted allyl alcohols are discussed.
