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Review
. 2023 Feb 1;28(3):1367.
doi: 10.3390/molecules28031367.

Recent Advances in the Synthesis of Cyclic Sulfoximines via C-H Bond Activation

Bingren Wang  1 , Xiayu Liang  1 , Qingle Zeng  1
Affiliations
Review

Recent Advances in the Synthesis of Cyclic Sulfoximines via C-H Bond Activation

Bingren Wang et al. Molecules. .

Abstract

Sulfoximines, a ubiquitous class of structural motifs, are widely present in bioactive molecules and functional materials that have received considerable attention from modern organic chemistry, pharmaceutical industries, and materials science. Sulfoximines have proved to be an effective directing group for C-H functionalization which was widely investigated for the synthesis of cyclic sulfoximines. Within the last decade, great progress has been achieved in the synthesis of cyclic sulfoximines. Thus, this review highlights the recent advances in the synthesis of cyclic sulfoximines via the C-H activation strategy and is classified based on the substrate types.

Keywords: C–H activation; cyclic sulfoximines; cyclization; synthesis; synthetic methods.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of bioactive cyclic sulfoximines and analogues.
Figure 2
Figure 2
The main strategies towards cyclic sulfoximines synthesis.
Scheme 1
Scheme 1
Rhodium-catalyzed annulation reactions for the synthesis of 1,2-benzothiazines.
Scheme 2
Scheme 2
Ir(III)-catalyzed C–H functionalization of sulfoximines with α-diazocarbonyl compounds.
Scheme 3
Scheme 3
Proposed mechanism of the formation of 1,2-benzothiazines in the Ir(III) catalytic system.
Scheme 4
Scheme 4
Synthesis of chiral-at-sulfur 1,2-benzothiazines via C–H functionalization of sulfoximines.
Scheme 5
Scheme 5
Proposed mechanism of Rh-catalyzed chiral-at-sulfur 1,2-benzothiazines formation.
Scheme 6
Scheme 6
Rhodium-catalyzed strategy for the enantiodivergent desymmetrization of sulfoximines.
Scheme 7
Scheme 7
Sustainable Rh(III)-catalyzed C–H activation/cyclization of sulfoximines to form 1,2-benzothiazines.
Scheme 8
Scheme 8
Proposed catalytic circle.
Scheme 9
Scheme 9
Rh(III)-catalyzed C–H functionalization strategy for the kinetic resolution of racemic sulfoximines.
Scheme 10
Scheme 10
Rh(III)-catalyzed method for the synthesis of fused 1,2-benzothiazines from sulfoximines and 4-diazoisochroman-3-imines.
Scheme 11
Scheme 11
Proposed mechanism of the annulation between sulfoximines and 4-diazoisochroman-3-imines.
Scheme 12
Scheme 12
Rh-catalyzed synthesis of highly conjugated 1,2-benzothiazine scaffolds.
Scheme 13
Scheme 13
Ir(III)-catalyzed C–H activation/annulation strategy for the synthesis of chiral 1,2-benzothiazines.
Scheme 14
Scheme 14
The synthesis of 1,2-benzothiazine through rhodium(III)-catalyzed annulative couplings.
Scheme 15
Scheme 15
Proposed mechanism of the tandem annulative coupling between sulfoximines and sulfoxonium ylides.
Scheme 16
Scheme 16
Desymmetrization, kinetic resolution, and parallel kinetic resolution of sulfoximines with sulfoxonium ylides under the Ru-catalyzed system.
Scheme 17
Scheme 17
Rhodium-catalyzed strategy for the synthesis of polycyclic 1,2-benzothiazines from different aryl sulfoximines and iodonium ylides.
Scheme 18
Scheme 18
Proposed mechanism of the reaction between sulfoximines and iodonium ylides.
Scheme 19
Scheme 19
Rhodium-catalyzed strategy for the synthesis of polycyclic 1,2-benzothiazines.
Scheme 20
Scheme 20
Ru(II)-catalyzed C–H functionalization strategy of sulfoximines for the enantioselective synthesis of 1,2-benzothiazines.
Scheme 21
Scheme 21
Proposed mechanism of Ru-catalyzed enantioselective synthesis of 1,2-benzothiazines.
Scheme 22
Scheme 22
Rh(III)-catalyzed C–H functionalization of sulfoximines to prepare dihydrobenzo thiadiazine 1-oxide derivatives.
Scheme 23
Scheme 23
Proposed mechanism of C–H functionalization of sulfoximines and annulation with benzyl azides.
Scheme 24
Scheme 24
Ir(III)-catalyzed amidation/cyclization for the C–H activation of sulfoximines with N-alkoxyamides to synthesize the corresponding thiadiazine 1-oxides.
Scheme 25
Scheme 25
Proposed catalytic cycle.
Scheme 26
Scheme 26
Rh(III)-catalyzed method to obtain benzothiadiazine-1-oxides using 1,4,2-dioxazol-5-ones.
Scheme 27
Scheme 27
Proposed mechanism.
Scheme 28
Scheme 28
Co(III)-catalyzed enantioselective C–N bond formation of cyclic sulfoximines.
Scheme 29
Scheme 29
Ru(II)/chiral-carboxylic-acid-catalyzed enantioselectivity synthesis of seven-membered cyclic sulfoximines.
Scheme 30
Scheme 30
The synthesis of 1, 2-benzothiazines in the Rh(Ⅲ) catalytic system using alkynyl silanes.
Scheme 31
Scheme 31
Proposed mechanism of annulation of sulfoximines and alkynyl silanes in the Rh catalytic system.
Scheme 32
Scheme 32
Tandem Rh(Ⅲ)-catalyzed C–H activation of sulfoximines to furnish furanone-fused 1,2-benzothiazines derivatives.
Scheme 33
Scheme 33
Pd(II)-catalyzed C–H functionalization strategy for the preparation of dibenzothiazines.
Scheme 34
Scheme 34
Proposed mechanism of Pd-catalyzed annulation of sulfoximines with arynes.
Scheme 35
Scheme 35
Metal-free method for the intramolecular C–N coupling to form benzothiazines.
Scheme 36
Scheme 36
Tandem C–H activation and C–N coupling of sulfoximines to form iodo-thiazines.
Scheme 37
Scheme 37
Metal-free tandem amination/bromination method for the synthesis of bromobenzothiazines.
Scheme 38
Scheme 38
DBH-promoted strategy for the cyclization of sulfoximines.
Scheme 39
Scheme 39
Pd/norbornene-catalyzed coupling reaction for the synthesis of fused polycyclic sulfoximines.
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