51157-80-3Relevant academic research and scientific papers
Formamide Catalysis Facilitates the Transformation of Aldehydes into Geminal Dichlorides
Huy, Peter Helmut
supporting information, p. 2474 - 2483 (2019/06/08)
Herein, a novel method for the transformation of aldehydes into geminal dichlorides based on phthaloyl chloride as reagent and N -formylpyrrolidine as Lewis base catalyst is disclosed. Given the mild reaction conditions, the current protocol is distinguished by high levels of functional group compatibility and scalability and is operationally simple. The in situ formation of a Vilsmeier Haack reagent type intermediate is likely to be essential for this organocatalytic nucleophilic substitution reaction.
Phosphorus(V)-catalyzed deoxydichlorination reactions of aldehydes
An, Jie,Tang, Xiaoping,Moore, Joshua,Lewis, William,Denton, Ross M.
, p. 8769 - 8776 (2013/09/23)
A phosphine oxide-catalyzed conversion of aldehydes into 1,1-dichlorides is reported. The reaction proceeds via a phosphorus(V)-catalysis manifold in which phosphine oxide turnover is achieved using oxalyl chloride as a consumable reagent. The new method is applicable to a range of aldehydes and, in combination with palladium-catalyzed reductive dimerization, gives rise to a new catalytic approach to the synthesis of stilbenes and a short formal synthesis of resveratrol.
Z-selective copper-catalyzed asymmetric allylic alkylation with grignard reagents
Giannerini, Massimo,Fananas-Mastral, Martin,Feringa, Ben L.
supporting information; experimental part, p. 4108 - 4111 (2012/04/10)
Allylic gem-dichlorides undergo regio- and enanantioselective (er up to 99:1) copper-catalyzed allylic alkylation with Grignard reagents affording chiral Z-vinyl chlorides. This highly versatile class of synthons can be subjected to Suzuki cross coupling affording optically active Z-alkenes and 1,3-cis,trans dienes.
