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Modular and Chemoselective Strategy for Accessing (Distinct) α,α‐Dihaloketones from Weinreb Amides and Dihalomethyllithiums
Author(s) -
Touqeer Saad,
Senatore Raffaele,
Malik Monika,
Urban Ernst,
Pace Vittorio
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001106
Subject(s) - chemistry , racemization , combinatorial chemistry , amide , halogen , modular design , optically active , organic chemistry , programming language , computer science , alkyl
The selective transfer of diversely functionalized dihalomethyllithiums (LiCHBrCl, LiCHClI, LiCHBrI, LiCHCl 2 , LiCHBr 2 , LiCHFI) to Weinreb amides for preparing gem‐ dihaloketones in one synthetic operation is reported. The capability of these amides as acylating agents and, the wide availability of dihalomethanes as pronucleophiles, enable a straightforward route to the title compounds under full chemocontrol. No racemization phenomena were evidenced in the case of optically active materials. Additionally, tolerance to sensitive functional groups (esters, amides, halogens, olefins etc .) was uniformly noticed, thus making this conceptually intuitive strategy flexible and tunable by the operator.