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1 d ortho-substituted arenes on the azomethine ylide.
2 t reported [3+3]-cycloaddition of a carbonyl ylide.
3 displacement of a nitro group or an iodonium ylide.
4 sfer to generate a more stable S-aryl sulfur ylide.
5 addition of the in situ generated azomethine ylide.
6 tropic rearrangement of an in situ generated ylide.
7 arrangement of a nitrile-stabilized ammonium ylide.
8 and by isolation of its trimethylphosphonium ylide.
9 ion present in the base used to generate the ylide.
10 aldehyde 19 with an amide-stabilized sulfur ylide.
11 e intramolecular syn-beta-elimination of the ylide.
12 enolide found in (1) via use of the Bestmann ylide.
13 he substitution pattern of the oxidopyrylium ylide.
14 ipolar cycloaddition chemistry of azomethine ylides.
15 nd 1,2,4-triazoles are precursors of nitrile ylides.
16 s/Sommelet-Hauser rearrangements of ammonium ylides.
17 Amines do not stabilize [3 + 2] ammonium-ylides.
18 phile-specific parameters N and sN for these ylides.
19 nd triflates with alpha-carbonyl sulfoxonium ylides.
20 lecules capable of being trapped by carbonyl ylides.
21 f aryl thiols and alpha-carbonyl sulfoxonium ylides.
22 tion of Michael acceptors with chiral sulfur ylides.
23 ddition reactions by and with the phosphorus ylides.
24 e advantageous safety profile of sulfoxonium ylides.
25 -substituted enoldiazo compounds with sulfur ylides.
26 s involves a catalytic asymmetric azomethine ylide 1,3-dipolar cycloaddition followed by an intramole
27 ck cyclization and intramolecular azomethine ylide 1,3-dipolar cycloaddition toward the total synthes
29 ophilicity parameters 4 < N < 8 for iodonium ylides 1(a-d) derived from these correlations show that
31 of the beta-dicarbonyl-substituted iodonium ylides 1(a-d) with several pi-conjugated carbenium and i
32 hesis include an enantioselective azomethine ylide (1,3)-dipolar cycloaddition reaction to set the ab
34 /tetrazolo[1,5-a]pyrazines generates nitrile ylides 15 via pyrazinylnitrenes 13 and triazacycloheptat
37 zirene (21): one (path a) leading to nitrile ylide (17) and the major products styrene and acetonitri
38 The reaction of cinnamaldehyde with iodonium ylide 1a catalyzed by (5S)-5-benzyl-2,2,3-trimethyl-imid
39 ne-derived iminium ion 10a with the iodonium ylide 1a with the rate constant calculated by eq 1 sugge
40 methanol with a 266 nm laser produces mainly ylide 2 (lambda(max) ~ 380 nm, tau ~ 6 mus, acetonitrile
42 show that the rate of the Wittig reaction of ylide 2 with aldehyde 14 is significantly faster than th
43 n of the stable ninhydrin-derived azomethine ylide [2-(3,4-dihydro-2 H-pyrrolium-1-yl)-1-oxo-1 H-inde
44 CH horizontal lineCH-Acc, 2) with pyridinium ylides 3, sulfonium ylide 4, and sulfonyl-substituted ch
45 s, including the formation of two azomethine ylides, [3 + 2]-cycloaddition, 1,3-sigmatropic rearrange
48 5-electrocyclization of the carbonyl nitrile ylide 4 and its structural nature (propargyl-like versus
50 -Acc, 2) with pyridinium ylides 3, sulfonium ylide 4, and sulfonyl-substituted chloromethyl anion 5.
51 intramolecular N-H insertion of sulfoxonium ylide 41 and conversion of ketone 32 to amine 31 in a si
54 a maximum at 320 nm due to the formation of ylide 8, which has a lifetime on the order of several mi
59 n-stabilised, semi-stabilised and stabilised ylides all occur under kinetic control by a common mecha
61 ized and used as the source of oxidopyrylium ylide, although the generality of this process remains u
62 tigating the synthesis of N-alkoxyazomethine ylides, an unexpected aminal byproduct was generated dur
64 polar cycloaddition with a simple azomethine ylide and a variety of vinyl fluorides and vinyl difluor
69 tituent, the reaction between the azomethine ylide and the alkene stops at the first step, leading to
71 from the corresponding beta-keto sulfoxonium ylides and anilines in the presence of TiCl(4) as a Lewi
74 cycloaddition reaction between oxidopyrylium ylides and cyclic imines with excellent control of regio
75 ddition reaction of nonstabilized azomethine ylides and cyclic N-sulfonyl imines has been developed p
76 rmation is nonreversible with semistabilized ylides and diastereoselectivities are determined in the
77 e in reactions of triphenylphosphine-derived ylides and has previously been observed for reactions un
78 n of HNO with triarylphosphines provides aza-ylides and HNO-derived amides, which may serve as stable
79 n, whereas the difference between azomethine ylides and imines is related to lower interaction energi
80 tion reactivities of 24 mesoionic azomethine ylides and imines were investigated using density functi
81 tegy exploited the diverse reactivity of aza-ylides and imines, and featured eight different macrocyc
82 ic (3 + 2) cycloadditions between azomethine ylides and nitroalkenes, followed by catalytic hydrogena
85 polar cycloaddition of stabilized azomethine ylides and sugar enones (dihydropyranones) derived from
86 -cycloaddition of enoldiazoacetates with aza-ylides and their selective coupling with nitrogen and ox
87 compounds to HNO (trapped as a phosphine aza-ylide) and the corresponding barbituric acid (BA) byprod
88 yclization partners (nucleophile, azomethine ylide, and dipolarophile), and further derivatization of
94 appendages of the approaching maltol-derived ylides are privileged by higher barriers for dimerizatio
95 [1,2]-sigmatropic rearrangements of ammonium ylides are studied by a combination of experimental, sta
96 s, provides proof of principle that iodonium ylides are suitable substrates for iminium-activated cyc
100 ongest superbases ever measured (phosphonium ylides) are reported, and by employing these compounds,
101 ishes the value of underutilized aziridinium ylides as key intermediates for converting small, strain
102 predicted azaquinone methides and azomethine ylides as the reactive intermediates and showed that imi
103 trated the utilization of fluorinated sulfur ylides as versatile reagents for Corey-Chaykovsky cyclop
106 pture in aprotic nucleophilic solvents (with ylide bands at 1625 cm(-1) in acetonitrile and 1586 and
110 bstituted enoldiazoacetates and imido-sulfur ylides by asymmetric [3+1]-cycloaddition using chiral sa
111 s of alpha-carbonyl-alpha'-amide sulfoxonium ylides by Pd/C-catalyzed carbonylative transformation of
112 lace via donation of electron density of the ylide carbon to the carbonyl carbon of benzaldehyde at a
113 thesis of increasing pyramidalisation of the ylide-carbon, highlighting the increasing dominance of E
114 mechanism while leaving behind the borenium ylide CB(11)(CH(3))(11), which is a strong Lewis acid an
116 ctions of all of the three major phosphonium ylide classes (non-stabilized, semi-stabilized, and stab
117 ybrids by reaction of N-metalated azomethine ylides [Cu(II) or Ag(I)] with the appropriate chiral lig
123 s with high ee and that stabilized sulfonium ylides (e.g., ester-stabilized) reacted with cyclic enon
124 ly been found that semi-stabilized sulfonium ylides (e.g., Ph-stabilized) reacted with cyclic and acy
129 omponent [3 + 2] cycloaddition of azomethine ylides followed by CuI-catalyzed cascade trifluoromethyl
130 ed heating they isomerize into 7a H-indolium ylides, followed by a barrierless 1,5-prototropic shift
131 wed by a highly stereoselective Cu-catalyzed ylide formation and then a [1,2]-Stevens rearrangement.
132 tion state involving a two-point attachment: ylide formation between the alcohol oxygen and the carbe
133 We provide direct spectroscopic evidence for ylide formation by singlet alpha-carbonyl carbene captur
134 t in tandem reactions, consisting of oxonium ylide formation followed by [2,3]-sigmatropic rearrangem
135 gmatropic rearrangement, as well as nitrogen ylide formation followed by azetidine ring expansion.
137 opropanation and subsequent ring expansions, ylide formation with subsequent rearrangements, and C-H
138 f five distinct steps: rhodium-bound oxonium ylide formation, [2,3]-sigmatropic rearrangement, oxy-Co
139 rogen insertion reactions, cyclopropanation, ylide formation, Wolff rearrangement, and cycloaddition
141 rated acetal leads to hyperolactone C, where ylide formation-rearrangement proceeds with high selecti
142 , cyclopropanation, cyclopropenation, sulfur ylide formation/2,3-sigmatropic rearrangement, as well a
144 erated from enoldiazoacetamides and carbonyl ylides formed from intramolecular carbene-carbonyl cycli
146 larophiles with in situ generated azomethine ylides from l-proline or acenaphthenequinone, formation
147 catalytic formation of versatile pyridinium ylides from metal carbenes has been poorly developed; th
148 are the precursors of N-metalated azomethine ylides from which up to four new chiral centers can be g
149 precedented substrate scope for the ammonium ylide functionality, and products are generated in high
150 methyl vinyl ketone (MVK): ketone-stabilized ylide gave 25% ee, ester-stabilized ylide gave 46% ee, a
151 abilized ylide gave 25% ee, ester-stabilized ylide gave 46% ee, and amide-stabilized ylide gave 89% e
153 ration of rGO via the addition of azomethine ylide generated from the ferrocenecarboxaldehyde oxime.
154 e of 1,3-dipolar cycloaddition of azomethine ylide generated in situ from ninhydrin and (thia)proline
156 +2] cycloaddition of unstabilized azomethine ylides generated from readily prepared trimethylsilyl-su
157 ycloaddition of 2 H-azirines with azomethine ylides generated in situ from isatins and alpha-amino ac
158 ugh the Stevens rearrangement of a sulfonium ylide, generated in situ from the coupling of a copper-c
159 tive 1,3-dipolar cycloaddition of azomethine ylides, generated from bis-aziridinedicarboxylate, to C6
162 his process is employed in a tandem ammonium ylide generation/[2,3]-rearrangement reaction, which for
163 yde is used in the presence of an azomethine ylide, giving the corresponding highly substituted pyrro
165 l theory), including previously unreported N(ylide)- H(cyclopropene) second-orbital interactions.
166 of the dimethyl triflate precursor with the ylide H2CPPh3 produced the mononuclear group 5 methylidy
168 addition reactions of N-metalated azomethine ylides has also been demonstrated by highly enantio- and
169 gioselective [2,3]-rearrangement of iodonium ylides has been developed as a general solution to catal
171 substrates using alpha-carbonyl sulfoxonium ylides has not been so far investigated, despite the pot
175 ly than the regioisomeric allomaltol-derived ylide (i.e., with a para methyl substitution relative to
176 r findings that maltol-derived oxidopyrylium ylides (i.e., with ortho methyl substitution relative to
177 tudy of the reaction between a novel type of ylide, i.e. nitrone ylides, and alkenes has been carried
178 n of a hydroxyquinone-derived phenyliodonium ylide in the presence of visible light using experiment
179 3-pyrrolyl BODIPY with different alkyl/aryl ylides in CH2Cl2 at room temperature for 2 h followed by
180 rearrangement of nitrile-stabilized ammonium ylides in conjunction with the reductive removal of the
181 reaction of vinyl benzoxazinones and sulfur ylides in good yields and good enantioselectivities.
183 rboxyl donor and the involvement of a unique ylide intermediate as the carboxyl acceptor in the CmoA-
186 f C-H activation, migratory insertion of the ylide into the carbon-metal bond, and protodemetalation,
188 The formation of the [3 + 2] phosphorus-ylide is exergonic, and hence, the [3 + 2] cycloaddition
190 arrangement of a nitrile-stabilized ammonium ylide is the key step of a very short and practical synt
191 -substituents in the case of semi-stabilized ylides is confirmed and is accommodated by the cycloaddi
193 pha-carbonyl-alpha'-(hetero)aryl sulfoxonium ylides is needed to benefit more greatly from the potent
194 cycloaddition of nitroalkenes and azomethine ylides is reported using a P,N-type ferrocenyl ligand an
196 A cascade sequence involving azomethine ylide isomerization followed by Mannich cyclization form
198 a diazo ketone, with an ether to produce an ylide-like intermediate that rearranges to produce E- or
200 benzyl ether derivative to asymmetric sulfur ylide-mediated epoxidation with up to 92% ee (14 example
202 from the polarization of the P=C bond in the ylide (n(O) -> pai(P=C)(*)), clamps the P=C and C=O bond
203 with azides, nitrones, azomethine imines and ylides, nitrile oxides, diazo compounds, and other dipol
204 -dienoate as a dipolarophile with azomethine ylides, nitrones, and nitrile oxides in good yields.
205 Thermal decomposition of the phenyliodonium ylide of lawsone gives rise to a highly reactive cyclic
206 de-mediated reaction between cyclic iodonium ylides of 1,3-dicarbonyls and 3-alkylidene-2-oxindoles r
207 initial electrophilic attack of the iodonium ylide on the C(beta) position of the diphenylketene, fol
210 e cyclizations of alpha-carbonyl sulfoxonium ylides onto benzenes, benzofurans and N-p-toluenesulfony
211 lar cycloadditions of N-metalated azomethine ylides onto C60 yielding a full stereodivergent synthesi
212 as a four-atom component, and Corey's sulfur ylide or ethyl bromoacetate acts as a one-atom carbon so
214 nt H(2)CPPh(3) (4 equiv) provides phosphorus ylide [P(3)O(8)CHPPh(3)](2-) (5) in 61% yield as a mixed
218 hanism of the reactions of formyl-stabilized ylide Ph3P horizontal lineCHCHO (1) and acetyl-stabilize
219 rizontal lineCHCHO (1) and acetyl-stabilized ylide Ph3P horizontal lineCHCOMe (2) with benzhydrylium
224 e 1,3-dipolar cycloaddition of an azomethine ylide (Prato reaction) with M(3)N@I(h)-C(80) (denoted as
225 f (18)F-FPEB was achieved by reaction of the ylide precursor (4 mg) with (18)F-Et4NF in dimethylforma
228 method that uses a hypervalent iodonium(III) ylide precursor, to prepare the radiopharmaceutical (18)
229 use of a new trifluoromethylated azomethine ylide precursor, which leads to a series of fluorinated
232 A cyclic beta-dicarbonyl phenyliodonium ylide reacted with various substituted styrenes under Rh
235 d stereospecifically into a variety of onium ylide rearrangement products, as well as compounds that
239 ig reaction, regardless of the nature of the ylide, regardless of the nature of the transition state,
240 rect formation of the corresponding carbonyl ylide resulted from the electrophilic addition of diamin
241 ar cycloaddition of unsymmetrical azomethine ylide resulting from the thermal C-C bond cleavage of un
242 derivatives and in situ generated azomethine ylide resulting in the formation of the pyrrolidine ring
243 lidene-5'-deoxy-5'-uridylaldehyde using this ylide results in a 3'-deoxy-3',4'-didehydronucleotide de
244 the azirinium ylide to metal-free azirinium ylide, ring-opening of the latter to give a 1,5-diazahex
245 the formation of a methyl triflate-based pre-ylide salt that upon treatment with base in the presence
246 t method that relies on spirocyclic iodonium ylide (SCIDY) precursors for one-step and regioselective
248 Furthermore, a clear correlation of ee with ylide stability was observed in reactions with methyl vi
249 rimental findings reveal that the azomethine ylide stabilized by an allylic group cycloadds to [60]fu
252 This species, or its corresponding sulfur ylide, subsequently adds into the substrate, initiating
254 to substitutions on both the alkylidene and ylide substrates and provided access to 19 new, densely
256 in the synthesis of this classical arsonium-ylide that have historically impeded its wider study.
257 [2,3]- and [1,2]-rearrangements of iodonium ylides that are controlled by copper catalysts bearing d
258 and convenient entry to reactive azomethine ylides that can (1) be protonated and reduced with high
259 esilylation provides endocyclic unstabilized ylides that successfully undergo cycloaddition with a ra
260 esilylation generates exocyclic unstabilized ylides that undergo cycloaddition with unsymmetrical alk
261 desilylated to give endocyclic unstabilized ylides that undergo intermolecular cycloadditions with c
262 nt Michael-addition approaches of the sulfur ylide, the transition state (TS) energies for the format
264 eds through formation of a vinyl aziridinium ylide; this reactive intermediate undergoes a pseudo-[1,
265 of the metal-bound complex of the azirinium ylide to metal-free azirinium ylide, ring-opening of the
266 e intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecul
267 benzylidineiminoglycinate-derived azomethine ylides to beta-silylmethylene malonates catalyzed by a A
268 ile at the nucleophilic carbon center of the ylides to give iodonium ions, which rapidly expel iodobe
271 ted to the same conditions, both addition of ylide trapping reagents and net isomerization of cis to
272 The reaction appears to proceed through an ylide-type mechanism, where the unique strain and struct
273 an effect that is common to reactions of all ylide types strongly argues for the operation of a commo
276 Yet, the rearrangement reactions of onium ylides via gold catalyzed carbene transfer reactions are
277 h in situ generated nonstabilized azomethine ylides via the domino Mannich reaction-dipolar cycloaddi
278 the formation of a nonstabilized azomethine ylide was developed by photoinduced reaction catalyzed w
280 g reaction of anisaldehyde with a stabilized ylide was studied by a combination of (13)C kinetic isot
282 have stable resonance contributions from aza-ylides were formed by using the nonhydrolysis Staudinger
284 a hydrogen acceptor, such as the phosphorus ylide, when combined with the alkylidene complex (PNP)Ti
285 dium hydroxide regenerated the corresponding ylide, which underwent a spontaneous intramolecular Witt
286 sters to generate metal-coordinated iodonium ylides, which undergo [2,3]-rearrangements with high sel
288 tions (1,3-DCs) of isatin-derived azomethine ylide with allenes have been established, which efficien
289 ect 1,3-dipolar cycloadditions of azomethine ylide with frequently used arylidene/alkylidene malonate
291 pyridinium, isoquinolinium, and quinolinium ylides with acceptor substituted dipolarophiles (arylide
292 reaction of these mixed phosphonium-iodonium ylides with acetylenes opens a way to new furyl annelate
294 nstants k2 for the reactions of the iodonium ylides with benzhydrylium ions correlate linearly with t
295 the cross-coupling reactions of sulfoxonium ylides with C(sp(2) )-H bonds of arenes and heteroarenes
296 pyridinium, isoquinolinium, and quinolinium ylides with diarylcarbenium ions, quinone methides, and
297 e reaction of beta-dicarbonyl phenyliodonium ylides with diphenylketene at room temperature affords m
298 semistabilized, and nonstabilized phosphorus ylides with various carbonyl compounds in the presence o
299 O quantitatively (trapped as a phosphine aza-ylide) with half-lives spanning 3 orders of magnitude (m
300 heteroaryls using alpha-carbonyl sulfoxonium ylides without the help of a directing group has remaine