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Ligand‐Controlled Regiodivergent Hydroalkylation of Pyrrolines
Author(s) -
Qian Deyun,
Hu Xile
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201912629
Subject(s) - regioselectivity , combinatorial chemistry , scope (computer science) , ligand (biochemistry) , hydride , chemistry , alkylation , catalysis , computer science , organic chemistry , biochemistry , receptor , metal , programming language
Nickel hydride (NiH) catalyzed hydrocarbonation has emerged as an efficient approach to construct new C−C bonds containing at least one C(sp 3 ) center. However, the regioselectivity of this reaction is by far dictated by substrates. Described here is a strategy to achieve two different regioselectivites of hydroalkylation of the same substrates by using ligand control. This strategy enables the first regiodivergent hydroalkylation of 3‐pyrrolines, yielding both 2‐ and 3‐alkylated pyrrolidines, valuable synthetic intermediates and common motifs in many bioactive molecules. This method demonstrates broad scope and high functional‐group tolerance, and can be applied in late‐stage functionalizations.