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Preparation of Solid Polyfunctional Alkynylzinc Pivalates with Enhanced Air and Moisture Stability for Organic Synthesis
Author(s) -
Chen YiHung,
Tüllmann Carl Phillip,
Ellwart Mario,
Knochel Paul
Publication year - 2017
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.201704400
Subject(s) - reagent , reactivity (psychology) , moisture , yield (engineering) , chemistry , decomposition , carbon fibers , zinc , organic synthesis , organic chemistry , combinatorial chemistry , chemical engineering , inorganic chemistry , materials science , catalysis , metallurgy , medicine , alternative medicine , pathology , composite number , composite material , engineering
We report the preparation of solid and air‐stable polyfunctionalized alkynylzinc pivalates from the corresponding alkynes using TMPZnOPiv (TMP=2,2,6,6‐tetramethylpiperidyl) as base. These organozinc pivalates are obtained as powders under mild conditions in excellent yields and can be manipulated in air for several hours without significant decomposition. These zinc reagents show an excellent reactivity in various carbon–carbon bond‐ forming reactions and 1,3‐dipolar cycloadditions. An alkynylzinc pivalate has been used to prepare a carboxyamidotriazole with potential antineoplastic activity in eight steps and 38 % overall yield.