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1 a heterocycle, or an unprotected alcohol or alkyne.
2 ine arising from reaction with the analogous alkyne.
3 ous catalyzed hydrometalation of olefins and alkynes.
4 /hydroamination cascade of readily available alkynes.
5 catalystic steps from commercially available alkynes.
6 enzannulation through difunctionalization of alkynes.
7 catalysts reported for the hydroamination of alkynes.
8 nerated by reaction of B(C(6) F(5) )(3) with alkynes.
9 d hydroboration of a variety of nitriles and alkynes.
10 semi- and complete hydrogenation of terminal alkynes.
11 arylative radical annulation reactions with alkynes.
12 es by avoiding challenging isolation of free alkynes.
13 yl ylides with a wide variety of alkenes and alkynes.
14 versatile fragment coupling approach toward alkynes.
15 theses, giving access to a broad spectrum of alkynes.
16 -mediated oxidative 1,2-amino-oxygenation of alkynes.
17 old-catalyzed oxidative coupling of terminal alkynes.
18 dependencies, i.e., internal versus terminal alkynes.
19 he first trans phosphinoboration of internal alkynes.
20 conditions worked well with both alkenes and alkynes.
21 n as surrogates for p-substituted arenes and alkynes.
22 e synthesis via carbene transfer to internal alkynes.
26 10,11), cyano(12), diazo(13), alkene(14) and alkyne(15-17) groups, continue to be discovered in natur
28 on of a terminal alkene to a monosubstituted alkyne; (2) a catalytic S(N)2'- and enantioselective all
30 yzed addition of terminal alkyne to acceptor alkyne, a Mukaiyama aldol reaction, a Yamaguchi esterifi
34 unctionality at position 2 of the adenine (2-alkyne adenosine or 2YnAd) is suitable for selective enr
36 clocondensation of primary nitroalkanes with alkynes/alkenes to afford a library of isoxazole/isoxazo
42 gy for heterobifunctional electron-deficient alkynes allowing for facile functionalization of payload
43 a a molecular shuffling process involving an alkyne, an alpha,beta-unsaturated acid chloride, which s
44 spired approach the so-derived cytospolide D alkyne analogue has been further converted to bicyclic a
45 cycle-mediated intramolecular coupling of an alkyne and a 1,3-diketone can proceed with a highly func
47 l alkanes, alkane isomers, and alkane/alkene/alkyne and C(8) alkylaromatics, with a particular focus
49 eactant structure and coupling a hydrophilic alkyne and hydrophobic azide results in a more pronounce
51 tion and olefination of dimedone establishes alkyne and vinylarene functionality linked by a neopenty
52 , carbon monoxide (carbonylation of terminal alkynes and alkenes), and other substrates will be discu
55 he Au(I)-catalyzed reaction between terminal alkynes and aromatic haloalkynes proceeds through diverg
56 f acylimines (in situ formed) with activated alkynes and aromatic nucleophiles such as indoles, pyrro
57 served "uptake mode", binding small-molecule alkynes and azides inside a water-soluble amphiphilic po
58 were produced from simple alkyl-substituted alkynes and Bu(3)SnH in high yield and good regioselecti
60 ic organic molecules, such as arynes, cyclic alkynes and cyclic allenes, have intrigued chemists for
61 ions, Ni@FAU showed remarkable adsorption of alkynes and efficient separations of acetylene/ethylene,
62 indicate the syn addition of Bu(3)SnH to the alkynes and imply the involvement of Sn-H bond activatio
65 tary linker functionalities (i.e., azide and alkyne) and follow-up attachment of stopper groups provi
69 rminal alkynes, dialkyl-substituted internal alkynes, and alkynes with electron-deficient substituent
70 nctional groups (including amides, nitriles, alkynes, and arenes) into the sp(3) -rich heterocyclic s
71 of alpha-keto aldehydes, anilines, activated alkynes, and aromatic nucleophiles is developed to synth
72 an electrochemical hydrogenation of alkenes, alkynes, and ketones using ammonia as the hydrogen sourc
73 -catalyzed addition of P-H bonds to alkenes, alkynes, and other unsaturated substrates in hydrophosph
74 romagnesiation of terminal alkenes, internal alkynes, and styrene derivatives, the underlying mechani
75 actions for the desymmetrization of alkene-, alkyne- and allene-tethered cyclohexadienones using tran
78 njugation reactions and reveal that strained alkynes are better reaction partners for achieving maxim
81 e organic compounds (e.g., alkanes, alkenes, alkynes, aromatics, carbonyls, and polycyclic aromatic h
83 namide-SAM conjugate (named NS1) features an alkyne as a key design element that closely mimics the l
85 ther, this work illustrates the potential of alkynes as latent electrophiles in small molecule inhibi
86 r accommodate a variety of internal aromatic alkynes as substrates for cyclopropenation with unpreced
88 uggests that the enhanced reactivity of bent alkynes, as compared to linear C=C triple bonds, finds i
91 lead but still relied on the Cu(I)-catalyzed alkyne-azide [3 + 2] cycloaddition for conjugation onto
92 erforms highly efficient copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) reactions on both alk
93 ysteine and can be used for copper-catalyzed alkyne-azide cycloaddition (CuAAC) without further proce
95 amenable to cluster-surface strain-promoted alkyne-azide cycloaddition chemistry with a strained cyc
96 ring-closing metathesis and copper-catalyzed alkyne-azide cycloaddition, peptide chemists embraced tr
104 dence that the copper catalyst activates the alkyne by hydrocupration, which controls both the regio-
105 -yielding Sonogashira coupling with volatile alkynes by avoiding challenging isolation of free alkyne
107 ilyl)acetylene Me3SiC2SiMe3 (mono-functional alkynes: C[triple bond, length as m-dash]C) in Cp'2M(eta
108 ctionalized molecules: Amines, alcohols, and alkynes can be attached onto the small malonate core uni
109 her a protected carbonyl or a functionalized alkyne, can be cyclized to the pyrrolodiketopiperazine b
111 tructural features: tert-butyl wheels, short alkyne chassis, and combination sets of wheels including
112 de-bond formation or a Cu(I)-catalyzed azide-alkyne click (CuAAC) reaction for labeling an octreotide
113 synthesized, followed by a step-growth azide-alkyne "click" reaction between the 4th-generation diazi
114 catalytic cycles, such as gold(III) alkene, alkyne, CO and hydride complexes, and important catalysi
115 New electrophiles and their corresponding alkyne conjugates were profiled directly in cultured cel
116 between hydrogen bonding and protonation of alkynes connected, on one side, to various aromatic ring
118 on of a unique pathway to produce a terminal alkyne-containing amino acid in the bacterium Streptomyc
119 Au complexes toward the polycondensation of alkyne-containing comonomers and heteroarene nucleophile
122 efficiency of the ruthenium-catalysed alkene-alkyne coupling reaction between readily available vinyl
125 The transit from early cycloadditions and alkyne couplings as ring-closing steps to very recent 3d
126 assembled through silver-catalyzed internal alkyne cyclization, and one-pot C-O bond cleavage/C-N bo
128 that remain challenging to prepare by azide-alkyne cycloaddition (AAC, CuAAC, RuAAC) methods and can
129 ity as ligands in copper-catalyzed azide and alkyne cycloaddition (CuAAC) reactions were studied.
131 generated in situ by copper-catalyzed azide-alkyne cycloaddition (CuAAC), providing interpenetrating
135 nylalanine via the copper(I)-catalyzed azide-alkyne cycloaddition can increase the conformational sta
136 thogonal hydrazide and copper-assisted azide-alkyne cycloaddition conjugation chemistries were employ
138 gen heterocycles was demonstrated with azide-alkyne cycloaddition to N-bromotetrafluoroethyl 1,2,3-tr
142 catalyst location on copper-catalyzed azide-alkyne cycloadditions which drive the self-reproduction
144 exhibited saturation-like behavior, whereas alkyne demonstrated a complex dependency; rate inhibitio
147 vely promoting the noncopper catalyzed azide-alkyne dipolar cycloaddition click reaction between eith
148 cinol derivatives with terminal and internal alkynes directed by picolinamide auxiliary has been deve
151 Current approaches to introduce terminal alkynes for bioorthogonal reactions into biomolecules st
153 w that an adenosine analogue with a terminal alkyne functionality at position 2 of the adenine (2-alk
156 Here we report a gram-scale synthesis of an alkyne-functionalized expanded [11]helicene and its sing
157 Highly efficient oxidative annulation of alkynes furnished diversely substituted pyran[2,3,4- de]
158 alpha-silylaryl triflates, Schiff bases, and alkynes generated polysubstituted pyrroles in good yield
159 ubstituted alkene equivalents to couple with alkynes, generating various boryl-substituted homoallyli
160 analog of puromycin that contains a terminal alkyne group, has facilitated the quantification of prot
161 ,6-Cl(2)C(6)H(3)) forms upon reaction of the alkyne H-C=CAr with the copper(II) tert-butoxide complex
162 ionalization of benzylic substrates R-H with alkynes H-C=CR' (R' = (hetero)aryl, silyl) that provide
165 e ruthenium catalytic addition of alkenes to alkynes has been demonstrated as a powerful synthetic to
169 ctive catalysts for ortho-hydroarylations of alkynes have previously been reported to result from act
170 tructurally different alkenes, along with an alkyne, have been utilized as dienophiles to afford a wi
171 m-dash]C, SiH) and alpha-di-SiH-substituted alkynes (hetero-tri-functional: SiH, C[triple bond, leng
172 several functional groups including terminal alkyne, heterocycle through click reaction, and others.
173 action, followed by either an intramolecular alkyne hydroarylation and subsequent alkene isomerizatio
176 yhydric alcohols, selective hydrogenation of alkynes, hydrogenation of nitroaromatics, CO(2) hydrogen
177 demonstrating divergent regioselectivity for alkyne hydrostannylation controlled by Cu/Fe vs Cu/Mn pa
179 the influence of the strained nature of the alkyne in their structures as well as the size of the sy
180 The challenging annulations of two different alkynes in a regioselective fashion have been demonstrat
181 ic dipole class, the electrophilicity of the alkynes in SNO-OCTs can be manipulated to achieve diverg
182 a concurrent oxidation of both aldehydes and alkynes in the course of their connection offers aroylox
183 c monomer (M) was prepared with two terminal alkynes in the outer rim for polymerization, and two ter
185 ns were suitable for a diverse collection of alkynes, including several highly functionalized pharmac
186 ey reactions involved in this annulation are alkyne insertion and aza-Michael addition under oxidant-
187 ed route to a truncated analogue carrying an alkyne instead of the natural n-pentyl side chain has be
188 ermediates from benign and readily available alkynes instead of hazardous diazo carbonyl compounds.
189 upported by Y, Lu, and La form the Ni(eta(2)-alkyne) intermediate, (eta(2)-PhC=CPh)Ni((i)Pr(2)PCH(2)N
191 he reaction of a Lewis acidic borane with an alkyne is a key step in a diverse range of main group tr
193 In contrast, a sulfonyl, ester-substituted alkyne is reactive enough that it couples with an azide
195 tly discovered gem-hydrogenation of internal alkynes is a fundamentally new transformation, in which
196 rential dihydrofunctionalization of terminal alkynes is accomplished through the reductive three-comp
200 ed a specific bioorthogonal probe, itaconate-alkyne (ITalk), for quantitative and site-specific chemo
201 vo cellular production of halo-, alkene- and alkyne-labelled proteins and natural products from gluco
202 ion pathways for BrMn(CO)(5), e.g., terminal alkynes lead to the generation of Mn(I)-acetylide specie
203 cyclization involving a BOX-ZnI(2)-activated alkyne leads to the formation of various cyclopentenes i
204 ng bis-styryl-BTD were retained with a rigid alkyne linker rendering a probe insensitive to cis-trans
208 ic derivatives: (1) a figure-eight dimer via alkyne metathesis (also gram scale) and (2) two arylene-
211 -defined molybdenum alkylidyne catalysts for alkyne metathesis, which is distinguished by a tripodal
215 lar oxygen efficiently deprotonates terminal alkyne moieties of 1,3,5-tris(4-ethynylphenyl)benzene (E
218 s not correlate with electrophilicity of the alkyne moiety, indicative of a proximity-driven reactivi
219 ort the multicomponent oxidative coupling of alkynes, nitriles, and Ti imido complexes for the synthe
220 lving those macrocycles having more strained alkynes not only are more exothermic and exhibit lower a
221 gged with a fluorescent dye or biotin to the alkyne of the analog, which can then be used to detect i
222 rmally triply bonded diplumbyne analogues of alkynes of the general formula ArPbPbAr (Ar = terphenyl
224 Here, competing reactions of a prochiral alkyne on Ag(111): two-dimensional (2D) homochiral Glase
225 Moreover, two fluorophores that include an alkyne or an azide group at the end of the alkyl chain a
229 chemoselective hydroboration of nitriles and alkynes over other reducible functionalities for the fir
232 yethylene glycol linker, carrying a strained alkyne (PEG-BCN) and the second component is the azide-f
236 on Bronsted acid promoted benzannulation of alkyne precursors prepared by palladium-catalyzed cross-
237 es are unsatisfactory coupling partners with alkynes, presumably due to the increased steric hindranc
238 tes to BF(3)-activated aldehydes followed by alkyne-Prins cyclization, Friedel-Crafts reaction, and f
240 t-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regi
241 es [Tp'(CO)(2)M=Si-M(CO)(2)(PMe(3))Tp'] with alkynes R(1)C=CR(2) and were comprehensively analyzed by
243 polydiacetylenes with intrinsic ultrastrong alkyne Raman signals that locate in this region for orga
244 yleneamine groups by exploiting its terminal alkyne reactivity with common organic electrophiles.
245 achieve reductive 1,1-difunctionalization of alkynes remains an important, but largely unaddressed, s
246 atalyze the coupling of boronic acids and/or alkynes, representative multi-site metal-catalyzed react
247 lso evaluated: the Sonogashira coupling with alkynes resulted in unsymmetrically substituted triazole
248 nent coupling of Ti imidos with nitriles and alkynes, ring opening of 2-imino-2H-azirines, or direct
251 osilylation reaction of internal symmetrical alkynes, silicon electrophiles, and primary alkyl zinc i
257 ed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes
265 ation of an activated copper complex, so any alkyne that is activated by copper reacts rapidly with t
266 yzed-1,3-dipolar cycloaddition of azides and alkynes (the CuAAC or "click" reaction) as the protocol
267 y, secondary, and tertiary alkyl-substituted alkynes, thus demonstrating divergent regioselectivity f
268 opening, a Pd-catalyzed addition of terminal alkyne to acceptor alkyne, a Mukaiyama aldol reaction, a
270 eeds first with the coordination of Au(I) to alkyne to initiate the reaction with 1,5-H shift as a ra
271 lace via nucleophilic attack of the terminal alkyne to the C2 carbon of the activated haloalkyne, ass
272 ctance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid ad
273 zirconium-catalyzed hydroaminoalkylation of alkynes to access alpha,beta,gamma-substituted allylic a
274 for the regioselective hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluo
275 [2,3-b]pyridin-1-yl)benzamides with internal alkynes to afford N-isoquinolono-7-azaindole via the for
276 + 2] cycloaddition reactions with different alkynes to generate 1,2-oxaphosphete ions, which were is
277 onditions was validated for dioxygenation of alkynes to highly demanding labile synthons, 1,2-diketon
278 en readily available vinyl boronic acids and alkynes to provide unsymmetrical 3-boryl-1,4-diene reage
279 henium-catalyzed semihydrogenation of diaryl alkynes to the corresponding E-alkenes has been achieved
280 the catalytic hydrostannylation of terminal alkynes under mild conditions, with Markovnikov/anti-Mar
281 electivity was observed for aryl-substituted alkynes under the Cu/Fe-catalyzed conditions, affording
284 s significantly enhanced (up to ~10(4) fold) alkyne vibration compared to conventional alkyne Raman p
286 yze the cis haloalkynylation of the terminal alkyne, whereas introduction of a weakly basic triflate
287 occurred only in the presence of coordinated alkyne, which suggests operation of a concerted metalati
288 nitriles in the presence of strained alkenes/alkynes, which allows for the orthogonal labeling of thr
289 more effective for less-reactive alkenes and alkynes, why a large excess of TMSCF(3) (1) is required
291 adical carbo-cyclization/gem-diborylation of alkynes with a high functional group tolerance is presen
293 s, dialkyl-substituted internal alkynes, and alkynes with electron-deficient substituents were found
295 of iPr(3)SiC=CX (X = H, Cl) across internal alkynes with formation of 1,3-enyne or 1-chloro-1,3-enyn
296 tool in organic synthesis, the reactivity of alkynes with isoelectronic main-group R(2)E=O compounds
298 he union of N-alkylamines and trimethylsilyl alkynes, without the presence of an external oxidant and
299 ne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even u