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One‐pot acid‐free ferrocenylalkylation of azoles with α‐ferrocenyl alcohols: ferrocene‐based plant growth regulators and herbicide safeners
Author(s) -
Shevaldina Ekaterina V.,
Opredelennova Ksenia A.,
Chichvarina Olga A.,
Spiridonov Yury Ya.,
Smol'yakov Alexandr F.,
Dorovatovskii Pavel V.,
Moiseev Sergey K.
Publication year - 2019
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5228
Subject(s) - chemistry , alkylation , imidazole , ferrocene , nucleophile , sulfonylurea , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , medicine , electrode , insulin , electrochemistry , endocrinology
α ‐Ferrocenylalkylation of azoles or S ‐nucleophiles with FcCH(R)OH (Fc = ferrocenyl) can be accomplished under acid‐free conditions as one‐pot process via an intermediate formation of the α ‐ferrocenylalkyl carbonates FcCH(R)OC(O)OEt. The reaction allows the alkylation of acid sensitive substrates like imidazole derivatives or sodium N,N ‐diethyldithiocarbamate. The reaction with ambident azoles proceeds as the N ‐alkylation. Some α ‐ferrocenylalkyl azoles were found to exhibit plant growth stimulating or herbicidal effects on corn seeds or act as the herbicide safeners against sulfonylurea herbicides.