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Iron(II) Pincer‐Catalyzed Synthesis of Lactones and Lactams through a Versatile Dehydrogenative Domino Sequence
Author(s) -
PeñaLópez Miguel,
Neumann Helfried,
Beller Matthias
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201402967
Subject(s) - dehydrogenation , domino , pincer movement , intramolecular force , catalysis , chemistry , combinatorial chemistry , stoichiometry , sequence (biology) , atom economy , cascade reaction , organic chemistry , biochemistry
The synthesis of lactones and lactams by using iron(II) pincer‐catalyzed dehydrogenative methodology was developed. Starting from 1, n ‐diols or 1, n ‐amino alcohols, this domino transformation takes place through initial dehydrogenation of the substrates, subsequent intramolecular cyclization, and final oxidation to afford the desired products in good yields. The ability to access heterocycles of different sizes makes this protocol especially versatile, in which two consecutive oxidation reactions are performed without requiring an external oxidant. In this paper, we report the application of the Fe‐MACHO‐BH complex [carbonylhydrido(tetrahydroborato)[bis(2‐diisopropylphosphinoethyl)amino]iron(II)] in this atom‐efficient and environmentally benign process, for which molecular hydrogen is formed as the only stoichiometric side product.