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1 athesis mediated (prevalent with B-H and B-R electrophiles).
2 es, given that they are carriers of the p-QM electrophile.
3 idine to generate an iodoamine as the active electrophile.
4 e and the synthetic equivalent of an alcohol electrophile.
5 residue on the protein via reaction with an electrophile.
6 he Michael adduct to be captured by an added electrophile.
7 ics, first order in amine and first order in electrophile.
8 ase activation of a readily available sulfur electrophile.
9 cluding the use of an alpha-fluoroacrylamide electrophile.
10 ethyl-l-histidine (Pmh) moiety transfers the electrophile.
11 of the boron-bound oxygen atoms by a second electrophile.
12 enabled assessment of their reactivity with electrophile.
13 these species to react selectively with the electrophile.
14 s polar solvents, and larger halogens on the electrophile.
15 or enantioselective fluoride delivery to the electrophile.
16 procedure depending on the reactivity of the electrophile.
17 the nitrosonium ion (NO(+)) was the reactive electrophile.
18 C-H functionalization reaction from benzylic electrophiles.
19 nalized and/or challenging aliphatic allylic electrophiles.
20 lenes with N-H, C-H, and O-H nucleophiles or electrophiles.
21 chieved using MeI and methyl bromoacetate as electrophiles.
22 m amides followed by reaction with different electrophiles.
23 elevated temperatures, and/or activated aryl electrophiles.
24 lcyclopropyl boronate complexes activated by electrophiles.
25 but not between neutral and cationic organic electrophiles.
26 and is compatible with a wide range of allyl electrophiles.
27 ociative CS(N)Ar type of reactivity for aryl electrophiles.
28 ps or by reactions of alkenyl boronates with electrophiles.
29 the cross-coupled product upon reaction with electrophiles.
30 use of either aryl chlorides or bromides as electrophiles.
31 same intracellular site modified by reactive electrophiles.
32 pendent on the sequence of the activation of electrophiles.
33 arget of covalent drugs and bioactive native electrophiles.
34 Tanaka initiated investigations into silicon electrophiles.
35 cluding aryl, heteroaryl, alkenyl, and amino electrophiles.
36 creases their nucleophilic character towards electrophiles.
37 c inflammation typically produced by noxious electrophiles.
38 hile Suginome began the exploration of boron electrophiles.
39 reversible interactions with small-molecule electrophiles.
40 or alpha,beta-unsaturated lactones as carbon electrophiles.
41 ibed with strong one-electron reductants and electrophiles.
42 ave relied on combining ketone enolates with electrophiles.
43 nd-forming reactions using unactivated alkyl electrophiles.
44 into achieving selectivity between different electrophiles.
45 (hetero)arenes after quenching with various electrophiles.
46 cally required for the reaction of different electrophiles.
47 omplexes and acid chloride or acid anhydride electrophiles.
48 heterocyclic amine nucleophiles and carbonyl electrophiles.
49 phenol nucleophiles and terpene diphosphate electrophiles.
50 , but are unreactive toward a range of other electrophiles.
51 the direct reductive coupling of two carbon electrophiles.
52 ch was hitherto limited to the use of halide electrophiles.
53 alkylcarbastannatrane nucleophiles with acyl electrophiles.
54 trapped by proton or various carbonyl-based electrophiles.
55 rs and a range of C=O, C=S, S(=O)(2) and P=O electrophiles.
56 a-Morita-Baylis-Hillman reaction of hindered electrophiles.
57 re among the most abundant and stable carbon electrophiles.
58 efins, with imines, nitriles and related C-N electrophiles.
59 ndance DNA adducts induced by reactions with electrophiles.
60 ons to activate various pro-nucleophiles and electrophiles.
61 ents, organoboronic esters, and a variety of electrophiles.
62 ary amine followed by capping with different electrophiles.
63 ic thiolation of organostannanes with sulfur electrophiles.
64 ygen but reacts with simple nucleophiles and electrophiles.
65 rminal alkyne reactivity with common organic electrophiles.
66 edge, kinetic experiments indicated that the electrophiles 1-bromobutane or ClSiMe3 in Et2O reacted a
67 aster than did MtAhpE-SH with the unspecific electrophile 4,4'-dithiodipyridine, a disulfide that exh
68 elopment of a potent scavenger of dicarbonyl electrophiles, 5-ethyl-2-hydroxybenzylamine (EtHOBA), wa
70 s nucleophiles and aryl/alkenyl triflates as electrophiles, a broad range of mono-, di-, tri- and tet
71 ll known for their reactivity as Lewis acids/electrophiles, a feature that is exploited in many pharm
72 l studies and electrophysiology to show that electrophiles act through a two-step process in which mo
75 ido-2-deoxy-d-mannoses with primary triflate electrophiles afforded corresponding 2-azido-2-deoxy-bet
76 kinetic asymmetric transformation of allenyl electrophiles affords C-alkylation products in high regi
77 remained the privilege of the most reactive electrophiles, all of which are cationic (or even dicati
80 tment of the prehydrolysis intermediate with electrophiles also provided a library of P-chiral TPOs i
81 tion of carbon-carbon bonds between an alkyl electrophile and an alkyl nucleophile is a persistent ch
82 artners, chiral Lewis-base activation of the electrophile and light activation of the nucleophile, en
83 te complexes occurs with 1,4 addition of the electrophile and migrating group across the pai system.
84 eutics, we performed a large-scale screen of electrophile and non-covalent fragments through a combin
85 and C-C bonds from a series of masked ketone electrophiles and a wide range of conventional heteroato
86 ollowed by introduction of carbonyl or imine electrophiles and aldol reactions initiated via enone co
87 d substrate scope, with a range of different electrophiles and boronic esters being successfully empl
88 oss-coupling of azaallyls with vinyl bromide electrophiles and delivers allylic amines in excellent y
89 The reaction succeeds with aryl and vinyl electrophiles and is compatible with heterocyclic fragme
90 lity is expected to find use with many other electrophiles and nucleophiles leading to new cross-coup
92 -H functionalization reactions from benzylic electrophiles and show how new reactive modalities may b
94 e active toward the coupling of sp(3)-carbon electrophiles and that well-controlled, light-driven cou
96 nature of the products formed (lipid-derived electrophiles), and the biological targets and mechanism
99 of 2-pyridine nucleophiles with (hetero)aryl electrophiles, and ranges from traditional cross-couplin
100 nge of organolithiums and Grignard reagents, electrophiles, and vinylcyclopropyl boronic esters can b
101 t reactions (MCRs) involving olefins and C-N electrophiles are a powerful tool to rapidly build up mo
102 log k(2)(20 degrees C) = s(N)(N + E), where electrophiles are characterized by one parameter (E) and
103 ad range of nitrogen nucleophiles and carbon electrophiles are compatible coupling partners in this r
104 convergent cross-coupling reactions of alkyl electrophiles are emerging as a powerful tool in asymmet
105 Abundant blood proteins adducted by active electrophiles are excellent markers to predict the risk
106 used to predict whether their reactions with electrophiles are kinetically or thermodynamically contr
108 nol, but is due to the absence of a reactive electrophile as long as a significant fraction of cycloh
109 olylbenzenes into azacoronenes using bromine electrophiles as alternative coupling agents is shown to
110 o their high Lewis basicities toward neutral electrophiles as quantified through quantum chemically c
111 bond formation by an aryl sulfonyl fluoride electrophile at a tyrosine residue (Tyr-82) inhibits gua
112 e advent of cross-coupling chemistry, carbon electrophiles based on halides or pseudohalides were the
113 and suggests further investigation of lipid electrophile-based combinational therapies for TNBC.
114 sic S(N)2 reaction of an amine with an alkyl electrophile, both with respect to reactivity and to ena
115 react readily with carbonyls and imines (pi-electrophiles), but are unreactive toward a range of oth
116 el-catalyzed substitution reactions of alkyl electrophiles by organometallic nucleophiles, including
118 ling between 9-BBN borate complexes and aryl electrophiles can be accomplished with Ni salts in the p
119 polar crossover pathway wherein two distinct electrophiles can be added across an alkene in a highly
120 n between palladium catalysts and alkyl/aryl electrophiles can be controlled by an OEEF applied along
121 cks that remain among the most underutilized electrophile classes in transition metal catalysis.
122 of its concentration) with an excess of the electrophiles ClSiMe3, 1-bromobutane (n-BuBr), or 1-iodo
124 les, the cross-coupling of unactivated alkyl electrophiles containing beta hydrogens remains a challe
125 iations that release nucleophiles instead of electrophiles could also be stimulated by suitably sited
127 ate that a metallaphotoredox-catalyzed cross-electrophile coupling mechanism provides a unified metho
128 on nucleophiles is well developed, the cross-electrophile coupling of aryl chlorides with alkyl chlor
130 alytic protocol that enables the first cross-electrophile coupling of unactivated alkyl chlorides and
134 nexpensive ligand for nickel-catalyzed cross-electrophile couplings by screening a diverse set of pha
137 C621 in TRPA1 and mechanistic insights into electrophile-dependent conformational changes in TRPA1.
138 s the installation of vinylphosphonothiolate electrophiles directly on cysteine side chains within pe
139 to activate unsaturated pai-systems with the electrophiles-driven ring-opening reactions of furans, w
141 and phenoxide salts) and fluorine-containing electrophiles (e.g., acid fluoride, fluoroformate, benze
143 y of the initial attack of the amines at the electrophiles followed by rate-determining deprotonation
145 cific thiol reactivities constitute a better electrophile for rational chemical probe and therapeutic
147 Employing phenols and phenol derivatives as electrophiles for cross-coupling reactions has numerous
148 an expanded repertoire of cysteine-reactive electrophiles for efficient and diverse targeting of the
150 iolates as a new class of cysteine-selective electrophiles for protein labeling and the formation of
151 y related quinone methides, common reference electrophiles for quantifying nucleophilic reactivities,
152 ryl-fluorosulfates as valuable Lys-targeting electrophiles, for the design of inhibitors of both enzy
156 nd-forming reactions with allylpalladium(II) electrophiles generated from allylic tert-butyl carbonat
158 deployed, addressing the roles of catalyst, electrophile (halenium donor), and nucleophile in determ
160 ivity of beta-aminocarbonates as anisotropic electrophiles has been investigated with several phenols
161 of carbon nucleophiles with oxygen-centered electrophiles has been little explored outside of nucleo
162 catalytic carboxylation of unactivated alkyl electrophiles has reached remarkable levels of sophistic
163 ulfur trioxide-trimethylamine complex as the electrophile, has been employed for installation of a su
168 ic aromatic substitution (prevalent with B-X electrophiles); (ii) sigma-bond metathesis mediated (pre
170 ide group remains the predominantly employed electrophile in CKI development, with its incorporation
171 e alkyne to act as both a nucleophile and an electrophile in sequential one-pot transformations.
172 usive that the ribosome is able to accept an electrophile in the P site other than the carboxyl group
175 ield has evolved from the addition of carbon electrophiles in a manner similar to that of protonation
176 ived from pyrazolin-5-ones have been used as electrophiles in asymmetric Mannich reactions with pyraz
178 esents the first general use of iodo-BCPs as electrophiles in cross-coupling, and the first Kumada co
179 tions and offers a basis for differentiating electrophiles in cross-electrophile coupling reactions.
180 e sought to determine the role of dicarbonyl electrophiles in inflammation-associated carcinogenesis.
182 ates hindered acid chlorides to be selective electrophiles in noncoordinating solvents for condensati
183 The reaction is enabled by a unique class of electrophiles in palladium-norbornene cooperative cataly
184 lustrates the potential of alkynes as latent electrophiles in small molecule inhibitors, enabling the
185 or performance of ortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothi
186 that zinc homoenolates can react as carbonyl-electrophiles in the presence of nucleophilic amines to
187 ogen-, boron-, oxygen-, and phosphorus-based electrophiles in transition-metal catalyzed cross-coupli
188 s were alkylated with N-acryloyl-1H-pyrazole electrophiles in up to 93 % yield and with up to >99.5 %
190 delivery of two reducing equivalents and an electrophile, in the form of a hydride (H(-) = 2e(-) + H
192 are further functionalized by reaction with electrophiles including CO(2) and aldehydes, whereas CF(
193 The process tolerates a diverse range of electrophiles, including aryl, heteroaryl, alkenyl, and
194 uctant to afford a general entry to sulfenyl electrophiles, including valuable trifluoromethyl, perfl
196 xes, which are versatile intermediates whose electrophile-induced 1,2-metallate rearrangement chemist
197 t advances in the rapidly expanding field of electrophile-induced stereospecific 1,2-migration of gro
200 , we introduced an alkyne moiety as a latent electrophile into small molecule inhibitors of cathepsin
204 and DNA alkylation by endogenously produced electrophiles is associated with the pathogenesis of neu
206 amine-catalyzed reactions of aldehydes with electrophiles is often explained by simple steric argume
208 The reaction on 2-(2-nitrovinyl) phenol as electrophile lead, in excellent yields and enantioselect
209 bstitution reaction varies, depending on the electrophile leaving group, acid cofactor, and nucleophi
214 ) has enabled reactions of unactivated alkyl electrophiles not only limited to the traditional cross-
215 arly attractive as a means to explore latent electrophiles not typically used in medicinal chemistry
217 xperiments reveal that among all common aryl electrophiles only aryl triflates are competent in these
218 ng the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access int
219 nvolve the use of a reagent, activated as an electrophile, onto which nucleophile coupling results in
221 bviating the need to isolate either an alkyl electrophile or an alkylmetal, while still effecting an
222 ms by which TRPA1 recognizes and responds to electrophiles or cytoplasmic second messengers remain un
223 o be unreactive with the cycloheptyl bromide electrophile over the average turnover time of catalysis
224 ns of GSSH with the physiologically relevant electrophiles peroxynitrite and hydrogen peroxide, and w
225 on-hydride/carbonyl complexes that enable an electrophile-promoted hydride migration process, resulti
226 chiral nickel catalyst that couples racemic electrophiles (propargylic halides) with racemic nucleop
228 lief that halogen bond catalysts bind to the electrophile quinoline and activate it by lowering its L
229 onal studies provide the molecular basis for electrophile recognition by the extraordinarily reactive
230 A series of aryl, heteroaryl, and druglike electrophiles relevant to pharmaceutical applications we
235 versibly engaged by cyanoacrylamide fragment electrophiles, revealing the broad potential for reversi
237 vant proteins; however, our understanding of electrophile-sensitive cysteines in the human immune pro
240 ndamental biochemical knowledge of precision electrophile signaling may be harnessed to assist covale
241 , n-butyllithium, elemental selenium, and an electrophile source was developed to allow the synthesis
243 vides perspective on the use of heteroatomic electrophiles, specifically silicon-, nitrogen-, boron-,
246 sulfinate salt can be quenched with various electrophiles such as alkyl halides, epoxides, Michael a
247 allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and tri
248 nally significant site for adduction of soft electrophiles such as OA-NO(2) and suggests further inve
249 he protease catalytic triad, as well as mild electrophiles such as sulfonamide, urea, and carbamate.
251 ioselectively alkylated with very hindered C-electrophiles, such as neopentyl, secondary and tertiary
252 for the conversion of widely available inert electrophiles, such as phenol derivatives, into the corr
254 w (1'-fluoro)vinyl cation equivalent, and an electrophile that previously eluded synthesis, capture a
256 selectivity has been limited to couplings of electrophiles that bear a directing group or a proximal
257 orts have ensued to characterize alternative electrophiles that exhibit irreversible or reversibly co
258 vergent cross-couplings can be achieved with electrophiles that lack such features; specifically, we
260 reactivity can be minimized by using latent electrophiles that only become activated towards covalen
261 sulfuramidimidoyl fluorides, a class of weak electrophiles that undergo sulfur(VI) fluoride exchange
262 on of ketones and an acyl silane, classes of electrophiles that were previously unreactive toward add
263 partners involved: the donor glycoside (the electrophile), the activator (that generally provides th
265 vity differences between indazole and indole electrophiles, the latter of which was used in our previ
266 n of this transformation using aryl or vinyl electrophiles, there are few examples involving unactiva
267 synthesized by the reaction of the bivalent electrophile thiabicyclo[3.3.1]nonane dinitrate with a s
268 to facilitate detoxification of soft organic electrophiles through covalent binding at its cysteine (
269 atalytic strategies involving functionalized electrophiles, thus expanding the scope of accessible 3,
270 reversal of the role of the nucleophile and electrophile to form C-N, C-O, C-S and C-C bonds from a
271 ioselective metalation and quenching with an electrophile to furnish C6-substituted derivatives which
273 with bicyclo[1.1.0]butyl lithium, react with electrophiles to achieve the diastereoselective difuncti
274 n tackling challenging targets is the use of electrophiles to allow irreversible binding to the targe
276 locks with aryl aldehydes and other carbonyl electrophiles to deliver a range of unsaturated alcohol
277 -fluoro sulfates as likely the most suitable electrophiles to effectively form covalent adducts with
278 ted isocyanides are efficiently trapped with electrophiles to generate substituted isocyanides incorp
279 eophilicity, enabling addition to a range of electrophiles (tropylium, benzodithiolylium, activated p
282 patiotemporal response of the cell milieu to electrophiles, we have designed a fluorogenic BODIPY-acr
283 gly, fluorosulfates, a new emerging class of electrophiles, were used to construct the sulfamate core
284 lly involve increasing the reactivity of the electrophile, which increases the risk of off-target mod
285 ferent rates with the two enantiomers of the electrophile, which interconvert under the reaction cond
286 tic quantities of S-acylthiosalicylamides as electrophiles, which are rapidly intercepted by amine re
287 alytic system, a mild base, and triflates as electrophiles, which are readily available from inexpens
289 dazolium bond was exploited to generate acyl electrophiles, which further react with amines and alcoh
290 are diffusion-limited reactions with strong electrophiles, which give mixtures of products arising f
291 son pioneered the way in the use of nitrogen electrophiles, while Suginome began the exploration of b
292 challenge associated with coupling an inert electrophile with a reactive one is overcome using a mul
293 catalyzed reactions that join a heteroatomic electrophile with an in situ generated nucleophile.
294 omplexes are consumed upon reaction with the electrophile with concomitant generation of cross-couple
295 over, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents a
296 nd the influence of various nucleophiles and electrophiles with different degrees of fluorination.
297 ective C-O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is rep
298 -alkynylthioanisole substrate and the ClBcat electrophile, with activation parameters of DeltaG(doubl
299 s, each bearing a sulfuramidimidoyl fluoride electrophile, with human cell lysate, and the protein co
300 confined within the framework, it becomes an electrophile yielding Aldol-Tishchenko selectivity.