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@PHDTHESIS{Wen:713112,
author = {Wen, Jian},
othercontributors = {Bolm, Carsten and Enders, Dieter},
title = {{C}opper-catalyzed dealkylations and rhodium-catalyzed
{C}−{H} functionalizations of {NH}-sulfoximines},
school = {RWTH Aachen University},
type = {Dissertation},
address = {Aachen},
reportid = {RWTH-2018-00926},
pages = {1 Online-Ressource (III, 127 Seiten) : Illustrationen},
year = {2018},
note = {Veröffentlicht auf dem Publikationsserver der RWTH Aachen
University; Dissertation, RWTH Aachen University, 2018},
abstract = {In recent years, functionalizations of sulfoximines have
attracted much attention because of interesting biological
activities of the resulting products. For example, to novel
heterocycles. In this thesis, the three types of
functionalizations of NH-sulfoximines for the construction
of sulfonimidamides, 1,2-benzothiazine 1-oxides and
1,2-benzothiazepine 1-oxides are presented. Firstly,
copper-catalyzed dealkylation/amination sequences which
provides sulfonimidamides from NH-sulfoximines under an
atmosphere of dioxygen. A wide range of sulfoximines were
tolerated affording the corresponding products in moderate
to good yields. Mechanistic studies suggested the
involvement of radicals in both the C–S bond cleavage and
the formation of the new N–S bond. Then, 4-unsubstituted
1,2-benzothiazines were prepared from NH-sulfoximines and
allyl methyl carbonate by Rh(III)-catalyzed domino
allylation/oxidative cyclization. The reaction exhibited a
broad scope with respect to NH-sulfoximines. A plausible
mechanism was proposed, and chemical potential of the
products has been demonstrated by some functionalization
reactions. In the last part of the work, Rh(III)-catalyzed
[4 + 3] annulations of NH-sulfoximines with
α,β-unsaturated ketones leading to 1,2-benzothiazepine
1‑oxides was presented. For a wide range of substrates
with various functional groups, product were obtained in
moderate to good yields. A mechanistic scheme has been
proposed, and the oxidative cleavage of the double bond in
the heterocycle was demonstrated.},
cin = {152920 / 150000},
ddc = {540},
cid = {$I:(DE-82)152920_20140620$ / $I:(DE-82)150000_20140620$},
typ = {PUB:(DE-HGF)11},
doi = {10.18154/RWTH-2018-00926},
url = {https://publications.rwth-aachen.de/record/713112},
}