2 article(s) from Lipshutz, Bruce H
Pharmaceuticals possessing a silicon or boron atom.
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The first Cu-catalyzed C(sp3)–Si bond formation.
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Conversion of benzylic phosphate 6 to the corresponding silane.
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Conversion of alkyl triflates to alkylsilanes.
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Conversion of secondary alkyl triflates to alkylsilanes.
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Conversion of alkyl iodides to alkylsilanes.
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Trapping of intermediate radical through cascade reaction.
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Radical pathway for conversion of alkyl iodides to alkylsilanes.
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Conversion of alkyl ester of N-hydroxyphthalimide to alkylsilanes.
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Conversion of gem-dibromides to bis-silylalkanes.
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Conversion of imines to α-silylated amines (A) and the reaction pathway (B).
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Conversion of N-tosylimines to α-silylated amines.
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Screening of diamine ligands.
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Conversion of N-tert-butylsulfonylimines to α-silylated amines.
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Conversion of aldimines to nonracemic α-silylated amines.
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Conversion of N-tosylimines to α-silylated amines.
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Reaction pathway [A] and conversion of aldehydes to α-silylated alcohols [B].
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Conversion of aldehydes to benzhydryl silyl ethers.
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Conversion of ketones to 1,2-diols (A) and conversion of imines to 1,2-amino alcohols (B).
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Ligand screening (A) and conversion of aldehydes to α-silylated alcohols (B).
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Conversion of aldehydes to α-silylated alcohols.
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1,4-Additions to α,β-unsaturated ketones.
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1,4-Additions to unsaturated ketones to give β-silylated derivatives.
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Additions onto α,β-unsaturated lactones to give β-silylated lactones.
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Conversion of α,β-unsaturated to β-silylated lactams.
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Conversion of N-arylacrylamides to silylated oxindoles.
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Conversion of α,β-unsaturated carbonyl compounds to silylated tert-butylperoxides.
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Catalytic cycle for Cu(I) catalyzed α,β-unsaturated compounds.
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Conversion of p-quinone methides to benzylic silanes.
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Conversion of α,β-unsaturated ketimines to regio- and stereocontrolled allylic silanes.
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Conversion of α,β-unsaturated ketimines to enantioenriched allylic silanes.
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Regioselective conversion of dienedioates to allylic silanes.
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Conversion of alkenyl-substituted azaarenes to β-silylated adducts.
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Conversion of conjugated benzoxazoles to enantioenriched β-silylated adducts.
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Conversion of α,β-unsaturated carbonyl indoles to α-silylated N-alkylated indoles.
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Conversion of β-amidoacrylates to α-aminosilanes.
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Conversion of α,β-unsaturated ketones to enantioenriched β-silylated ketones, nitriles, and nitro d...
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Regio-divergent silacarboxylation of allenes.
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Silylation of diazocarbonyl compounds, (A) asymmetric and (B) racemic.
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Enantioselective hydrosilylation of alkenes.
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Conversion of 3-acylindoles to indolino-silanes.
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Proposed mechanism for the silylation of 3-acylindoles.
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Silyation of N-chlorosulfonamides.
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Conversion of acyl silanes to α-silyl alcohols.
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Conversion of N-tosylaziridines to β-silylated N-tosylamines.
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Conversion of N-tosylaziridines to silylated N-tosylamines.
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Conversion of 3,3-disubstituted cyclopropenes to silylated cyclopropanes.
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Conversion of conjugated enynes to 1,3-bis(silyl)propenes.
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Proposed sequence for the Cu-catalyzed borylation of substituted alkenes.
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Cu-catalyzed synthesis of nonracemic allylic boronates.
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Cu–NHC catalyzed synthesis of α-substituted allylboronates.
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Synthesis of α-chiral (γ-alkoxyallyl)boronates.
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Cu-mediated formation of nonracemic cis- or trans- 2-substituted cyclopropylboronates.
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Cu-catalyzed synthesis of γ,γ-gem-difluoroallylboronates.
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Cu-catalyzed hydrofunctionalization of internal alkenes and vinylarenes.
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Cu-catalyzed Markovnikov and anti-Markovnikov borylation of alkenes.
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Cu-catalyzed borylation/ortho-cyanation/Cope rearrangement.
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Borylﬂuoromethylation of alkenes.
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Cu-catalyzed synthesis of tertiary nonracemic alcohols.
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Synthesis of densely functionalized and synthetically versatile 1,2- or 4,3-borocyanated 1,3-butadi...
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Cu-catalyzed trifunctionalization of allenes.
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Cu-catalyzed selective arylborylation of arenes.
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Asymmetric borylative coupling between styrenes and imines.
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Regio-divergent aminoboration of unactivated terminal alkenes.
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Cu-catalyzed 1,4-borylation of α,β-unsaturated ketones.
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Cu-catalyzed protodeboronation of α,β-unsaturated ketones.
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Cu-catalyzed β-borylation of α,β-unsaturated imines.
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Cu-catalyzed synthesis of β-trifluoroborato carbonyl compounds.
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Asymmetric 1,4-borylation of α,β-unsaturated carbonyl compounds.
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Cu-catalyzed ACB and ACA reactions of α,β-unsaturated 2-acyl-N-methylimidazoles.
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Cu-catalyzed diborylation of aldehydes.
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Umpolung pathway for chiral, nonracemic tertiary alcohol synthesis (top) and proposed mechanism for...
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Cu-catalyzed synthesis of α-hydroxyboronates.
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Cu-catalyzed borylation of ketones.
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Cu-catalyzed borylation of unactivated alkyl halides.
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Cu-catalyzed borylation of allylic difluorides.
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Cu-catalyzed borylation of cyclic and acyclic alkyl halides.
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Cu-catalyzed borylation of unactivated alkyl chlorides and bromides.
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Cu-catalyzed decarboxylative borylation of carboxylic acids.
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Cu-catalyzed borylation of benzylic, allylic, and propargylic alcohols.
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Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67
Road map to enhanced C–H activation reactivity.
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Concerted metalation–deprotonation and elelectrophilic palladation pathways for C–H activation.
Routes for generation of cationic palladium(II) species.
Optimized conditions for C–H arylations at room temperature.
Biaryl formation catalyzed by Pd(OAc)2.
C–H arylation results. Conditions A: Conducted at rt for 20 h in 2 wt % Brij 35/water (1 mL) with 1...
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Monoarylations in water at rt. Conditions A: Conducted at rt for 20 h in 2 wt % Brij 35/water with ...
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Selective arylation of a 1-naphthylurea derivative.
Fujiwara–Moritani coupling rreactions in water. Conditions A: 10 mol % [Pd(MeCN)4](BF4)2, 1 equiv B...
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Optimization. Conducted at rt for 8 h or as otherwise noted in EtOAc with 10 mol % Pd catalyst, AgO...
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Representative results in EtOAc. Conducted at rt in EtOAc with 10 mol % Pd(OAc)2, HBF4 (1 equiv), a...
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Previous syntheses of boscalid®.
Synthesis of boscalid®. aConducted at rt for 20 h in EtOAc with 10 mol % [Pd(MeCN)4](BF4)2, BQ (5 e...
Hypothetical reaction sequence for cationic Pd(II)-catalyzed aromatic C–H activation reactions.
X-ray structure of palladacycle 6 with thermal ellipsoids at the 50% probability level. BF4 and hyd...
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NMR studies. A: The reaction of [Pd(MeCN)4](BF4)2 and 3-MeOC6H4NHCONMe2 in acetone-d6. B: The react...
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The generation of cationic Pd(II) from Pd(OAc)2.
Electrophilic substitution of aromatic hydrogen by cationic palladium(II) species.
Attempted reactions of palladacycle 6.
The impact of MeCN on C-H activation/coupling reactions.
Stoichiometric MeCN-free reactions. a2% Brij 35 was used instead of EtOAc.
The reactions of divalent palladacycles.
Role of BQ in stoichiometric Fujiwara–Moritani and Suzuki–Miyaura coupling reactions. aYields based...
Proposed role of BQ in Fujiwara–Moritani reactions.
Proposed role of BQ in Suzuki–Miyaura coupling reactions.
Stoichiometric C–H arylation of iodobenzene. aYields based on Pd.
Impact of acetate on the cationicity of Pd.
Roles of additives in C–H arylation.
Cross-coupling in the presence of AgBF4.
A proposed catalytic cycle for Fujiwara–Moritani reactions.
Proposed catalytic cycle of C–H activation/Suzuki–Miyaura coupling reactions.
A proposed catalytic cycle for C–H arylation involving a Pd(IV) intermediate.
Selected reactions of divalent palladacycles.
Beilstein J. Org. Chem. 2016, 12, 1040–1064, doi:10.3762/bjoc.12.99
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