Angewandte Chemie International Edition, ISSN 1433-7851, 11/2018, Volume 57, Issue 48, pp. 15841 - 15846
Despite a well‐developed and growing body of work in Cu catalysis, the potential of Cu to serve as a photocatalyst remains underexplored. Reported herein is...
cross-coupling | copper | peptides | radicals | photochemistry | ENDOMORPHIN-1 ANALOGS | N-HYDROXYPHTHALIMIDE ESTERS | CROSS-COUPLING REACTION | PHOTOREDOX | ALPHA | CHEMISTRY, MULTIDISCIPLINARY | AMINO-ACIDS | ALKYLMAGNESIUM HALIDES | REDOX-ACTIVE ESTERS | GRIGNARD-REAGENTS | N-(ACYLOXY)PHTHALIMIDES | Peptides | Glycine | Copper | Amino acids | Catalysis | Alkylation
cross-coupling | copper | peptides | radicals | photochemistry | ENDOMORPHIN-1 ANALOGS | N-HYDROXYPHTHALIMIDE ESTERS | CROSS-COUPLING REACTION | PHOTOREDOX | ALPHA | CHEMISTRY, MULTIDISCIPLINARY | AMINO-ACIDS | ALKYLMAGNESIUM HALIDES | REDOX-ACTIVE ESTERS | GRIGNARD-REAGENTS | N-(ACYLOXY)PHTHALIMIDES | Peptides | Glycine | Copper | Amino acids | Catalysis | Alkylation
Journal Article
Chemistry – A European Journal, ISSN 0947-6539, 07/2017, Volume 23, Issue 37, pp. 8814 - 8817
The functionalization of internal olefins has been a challenging task in organic synthesis. This protocol provides an efficient and transition‐metal‐free...
cross-coupling | alkylation | C−H activation | metal-free | internal olefins | DIRECT ALKENYLATION | ACTIVATION | EFFICIENT SYNTHESIS | TERMINAL ALKYNES | RADICAL CYCLIZATION CONDITIONS | CHEMISTRY, MULTIDISCIPLINARY | C-H BONDS | FUNCTIONALIZATION | C-H activation | 6-MEMBERED HETEROCYCLIC RINGS | HECK REACTION | ALKANES | Cross coupling | Alkenes | Hydrogen bonds | Metals | Scaling up | Chemical bonds | Alkanes | Cleavage | Substrates | Alkylation
cross-coupling | alkylation | C−H activation | metal-free | internal olefins | DIRECT ALKENYLATION | ACTIVATION | EFFICIENT SYNTHESIS | TERMINAL ALKYNES | RADICAL CYCLIZATION CONDITIONS | CHEMISTRY, MULTIDISCIPLINARY | C-H BONDS | FUNCTIONALIZATION | C-H activation | 6-MEMBERED HETEROCYCLIC RINGS | HECK REACTION | ALKANES | Cross coupling | Alkenes | Hydrogen bonds | Metals | Scaling up | Chemical bonds | Alkanes | Cleavage | Substrates | Alkylation
Journal Article
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, ISSN 1433-7851, 03/2019, Volume 58, Issue 12, pp. 4002 - 4006
The synthetic utility of tertiary amines to oxidatively generate a-amino radicals is well established, however, primary amines remain challenging because of...
radicals | ACIDS | amines | reaction mechanisms | ALPHA-AMINOALKYL RADICALS | CHEMISTRY, MULTIDISCIPLINARY | C-H BONDS | ATOM | FUNCTIONALIZATION | ABSTRACTION | photochemistry | ADDITION-REACTIONS | ARENECARBONITRILES | ALIPHATIC-AMINES | PHOTOCHEMICAL-REACTIONS | synthetic methods | Side reactions | Divergence | Amines | Alkenes | Sulfonamides | Selectivity | Catalysis | Derivatives | Amino radical | Alkylation | Intermediates
radicals | ACIDS | amines | reaction mechanisms | ALPHA-AMINOALKYL RADICALS | CHEMISTRY, MULTIDISCIPLINARY | C-H BONDS | ATOM | FUNCTIONALIZATION | ABSTRACTION | photochemistry | ADDITION-REACTIONS | ARENECARBONITRILES | ALIPHATIC-AMINES | PHOTOCHEMICAL-REACTIONS | synthetic methods | Side reactions | Divergence | Amines | Alkenes | Sulfonamides | Selectivity | Catalysis | Derivatives | Amino radical | Alkylation | Intermediates
Journal Article
Journal of the American Chemical Society, ISSN 0002-7863, 10/2017, Volume 139, Issue 42, pp. 14897 - 14900
Visible light photoredox catalysis enables direct γ- C(sp3)–H alkylation of saturated aliphatic carbonyl compounds. Electron-deficient alkenes are used as the...
FUNCTIONALIZATION | C(SP)-H BONDS | ACTIVATION | AMINATION | OLEFINATION | NITROGEN-CENTERED RADICALS | ARYLATION | CHEMISTRY, MULTIDISCIPLINARY | C-H BONDS
FUNCTIONALIZATION | C(SP)-H BONDS | ACTIVATION | AMINATION | OLEFINATION | NITROGEN-CENTERED RADICALS | ARYLATION | CHEMISTRY, MULTIDISCIPLINARY | C-H BONDS
Journal Article
Journal of the American Chemical Society, ISSN 0002-7863, 05/2014, Volume 136, Issue 19, pp. 6858 - 6861
Direct β-alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced...
OXIDATION | ORGANIC-SYNTHESIS | CATALYSIS | ACTIVATION | ASYMMETRIC CONJUGATE ADDITION | VISIBLE-LIGHT PHOTOCATALYSIS | ARYLATION | CARBOXYLIC ESTERS | RADICALS | MICHAEL ACCEPTORS | CHEMISTRY, MULTIDISCIPLINARY | Activated | Spectroscopy | Pathways | Spectroscopic analysis | Catalysis | Aldehydes | Radicals | Quenching | Communication
OXIDATION | ORGANIC-SYNTHESIS | CATALYSIS | ACTIVATION | ASYMMETRIC CONJUGATE ADDITION | VISIBLE-LIGHT PHOTOCATALYSIS | ARYLATION | CARBOXYLIC ESTERS | RADICALS | MICHAEL ACCEPTORS | CHEMISTRY, MULTIDISCIPLINARY | Activated | Spectroscopy | Pathways | Spectroscopic analysis | Catalysis | Aldehydes | Radicals | Quenching | Communication
Journal Article
Journal of the American Chemical Society, ISSN 0002-7863, 06/2016, Volume 138, Issue 25, pp. 8019 - 8030
Herein we describe our efforts to elucidate the key mechanistic aspects of the previously reported enantioselective photochemical α-alkylation of aldehydes...
VISIBLE-LIGHT | SOMO ACTIVATION | COMPLEX | ELECTRON-TRANSFER | ORGANOCATALYSIS | CHEMISTRY | RADICALS | SUBSTITUTION-REACTIONS | CHEMISTRY, MULTIDISCIPLINARY | 2+2 PHOTOCYCLOADDITION REACTIONS | PHOTOREDOX CATALYSIS | Chemical properties | Aldehydes | Analysis | Alkylation | Photochemistry | Trapping | Catalysts | Reaction kinetics | Chain reactions | Chains | Assessments | Radicals
VISIBLE-LIGHT | SOMO ACTIVATION | COMPLEX | ELECTRON-TRANSFER | ORGANOCATALYSIS | CHEMISTRY | RADICALS | SUBSTITUTION-REACTIONS | CHEMISTRY, MULTIDISCIPLINARY | 2+2 PHOTOCYCLOADDITION REACTIONS | PHOTOREDOX CATALYSIS | Chemical properties | Aldehydes | Analysis | Alkylation | Photochemistry | Trapping | Catalysts | Reaction kinetics | Chain reactions | Chains | Assessments | Radicals
Journal Article
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Full Text
Dioxygen‐Mediated Decarbonylative CH Alkylation of Heteroaromatic Bases with Aldehydes
Chemistry – A European Journal, ISSN 0947-6539, 12/2015, Volume 21, Issue 49, pp. 17618 - 17622
An operationally simple and economical method for the direct alkylation of heteroaromatic bases employing readily available aldehydes as alkyl radical...
auto‐oxidation | radical reactions | CH functionalization | heterocycles | oxygen | C-H functionalization | auto-oxidation | SUBSTITUTION | SECONDARY | BOND FORMATION | CHEMISTRY, MULTIDISCIPLINARY | FUNCTIONALIZATION | FREE-RADICAL REACTIONS | PHOTOCHEMICAL-REACTIONS | HOMOLYTIC ALKYLATION | DERIVATIVES | METAL-FREE | MOLECULAR-OXYGEN | Economics | Transformations | Aldehydes | Precursors | Radicals | Alkylation
auto‐oxidation | radical reactions | CH functionalization | heterocycles | oxygen | C-H functionalization | auto-oxidation | SUBSTITUTION | SECONDARY | BOND FORMATION | CHEMISTRY, MULTIDISCIPLINARY | FUNCTIONALIZATION | FREE-RADICAL REACTIONS | PHOTOCHEMICAL-REACTIONS | HOMOLYTIC ALKYLATION | DERIVATIVES | METAL-FREE | MOLECULAR-OXYGEN | Economics | Transformations | Aldehydes | Precursors | Radicals | Alkylation
Journal Article
Organic Letters, ISSN 1523-7060, 10/2018, Volume 20, Issue 20, pp. 6345 - 6348
The first Pd-catalyzed alkylation of (iso)quinolines and arenes is reported. The readily available and bench-stable 2-acylpyridine compounds were used as an...
ARYL BROMIDES | DIARYLMETHANES | FREE REGIOSELECTIVE ALKYLATION | PALLADIUM | CROSS-COUPLING REACTIONS | HETEROARENES | ALPHA-ARYLATION | CHEMISTRY, ORGANIC | PYRIDINE N-OXIDES | RADICAL ALKYLATION | ALKYLZINC HALIDES
ARYL BROMIDES | DIARYLMETHANES | FREE REGIOSELECTIVE ALKYLATION | PALLADIUM | CROSS-COUPLING REACTIONS | HETEROARENES | ALPHA-ARYLATION | CHEMISTRY, ORGANIC | PYRIDINE N-OXIDES | RADICAL ALKYLATION | ALKYLZINC HALIDES
Journal Article
Chemical Communications, ISSN 1359-7345, 2017, Volume 53, Issue 64, pp. 8964 - 8967
The catalytic asymmetric alkylation of the remote, unactivated delta-position of N-alkyl amides was enabled by the combination of visible-light-induced...
FUNCTIONALIZATION | ACTIVATION | AMINATION | COMPLEX | STRATEGY | IODINE | RADICALS | CHEMISTRY, MULTIDISCIPLINARY | C-H BONDS | PHOTOREDOX CATALYSIS
FUNCTIONALIZATION | ACTIVATION | AMINATION | COMPLEX | STRATEGY | IODINE | RADICALS | CHEMISTRY, MULTIDISCIPLINARY | C-H BONDS | PHOTOREDOX CATALYSIS
Journal Article
Nature, ISSN 0028-0836, 11/2016, Volume 539, Issue 7628, pp. 268 - 271
Despite advances in hydrogen atom transfer (HAT) catalysis(1-5), there are currently no molecular HAT catalysts that are capable of homolysing the strong...
CENTERED RADICALS | FUNCTIONALIZATION | OXIDATION | ABSTRACTION | MULTIDISCIPLINARY SCIENCES | ATOM-TRANSFER | CARBOXAMIDES | GENERATION | HYDROAMINATION | ENERGIES | CYCLIZATION | Alkylation - radiation effects | Protons | Alkenes - chemistry | Electron Transport | Amination | Nitrogen - chemistry | Oxidation-Reduction | Amides - chemistry | Catalysis - radiation effects | Hydrogen - chemistry | Iridium - chemistry | Carbon - chemistry | Chemical bonds | Catalysis | Nitrogen | Hydrogen | Carbon | Luminescence quenching
CENTERED RADICALS | FUNCTIONALIZATION | OXIDATION | ABSTRACTION | MULTIDISCIPLINARY SCIENCES | ATOM-TRANSFER | CARBOXAMIDES | GENERATION | HYDROAMINATION | ENERGIES | CYCLIZATION | Alkylation - radiation effects | Protons | Alkenes - chemistry | Electron Transport | Amination | Nitrogen - chemistry | Oxidation-Reduction | Amides - chemistry | Catalysis - radiation effects | Hydrogen - chemistry | Iridium - chemistry | Carbon - chemistry | Chemical bonds | Catalysis | Nitrogen | Hydrogen | Carbon | Luminescence quenching
Journal Article
Angewandte Chemie International Edition, ISSN 1433-7851, 06/2013, Volume 52, Issue 23, pp. 6080 - 6083
The apparent and the real: What looks like a Friedel–Crafts alkylation reaction of electron‐deficient pyrroles is actually a PdII‐catalyzed,...
alkylation | CH activation | palladium | homogeneous catalysis | heterocycles | C-H activation | 1,3-DICARBONYL COMPOUNDS | ALPHA,BETA-UNSATURATED ALDEHYDES | BOND FUNCTIONALIZATION | PYRRYLMAGNESIUM BROMIDE | ALKENE-PHOSPHINE LIGANDS | AROMATIC-SUBSTITUTION | CHEMISTRY, MULTIDISCIPLINARY | CH activation | ASYMMETRIC ALLYLIC ALKYLATION | FRIEDEL-CRAFTS ALKYLATION | RADICAL ALKYLATION | FUNCTIONALIZED PYRROLES | Activation | Derivatives | Alkylation | Pyrroles
alkylation | CH activation | palladium | homogeneous catalysis | heterocycles | C-H activation | 1,3-DICARBONYL COMPOUNDS | ALPHA,BETA-UNSATURATED ALDEHYDES | BOND FUNCTIONALIZATION | PYRRYLMAGNESIUM BROMIDE | ALKENE-PHOSPHINE LIGANDS | AROMATIC-SUBSTITUTION | CHEMISTRY, MULTIDISCIPLINARY | CH activation | ASYMMETRIC ALLYLIC ALKYLATION | FRIEDEL-CRAFTS ALKYLATION | RADICAL ALKYLATION | FUNCTIONALIZED PYRROLES | Activation | Derivatives | Alkylation | Pyrroles
Journal Article
The Journal of Organic Chemistry, ISSN 0022-3263, 06/2000, Volume 65, Issue 13, pp. 4101 - 4111
The synthesis of 1,2,8,8a-tetrahydrocyclopropa[c]pyrrolo[3,2-e]indol-4(5H)-one (CPI), the parent CC-1065 and duocarmycin SA alkylation subunit, is detailed....
ARYL RADICAL CYCLIZATION | ANTITUMOR ANTIBIOTICS | STREPTOMYCES SP | SITE MODELS | PYRINDAMYCIN-A | ANALOGS | ENT-(-)-DUOCARMYCIN SA | BINDING SUBUNIT | CHEMISTRY, ORGANIC | VINYL-CHLORIDE | LINKING AMIDE | Molecular Conformation | Oligodeoxyribonucleotides - chemistry | Models, Molecular | Crystallography, X-Ray | Alkylation | Alkylating Agents - chemistry | DNA, Viral - chemistry | DNA - chemistry | Quinolones - chemistry | Antibiotics, Antineoplastic - chemistry | Quinolones - chemical synthesis | Base Sequence | Pyrroles - chemistry | Indicators and Reagents | Molecular Structure | Indoles | Leucomycins - chemistry | Indolequinones | Research | Catalysis | Alkylating agents | Analysis | Structure-activity relationships (Biochemistry)
ARYL RADICAL CYCLIZATION | ANTITUMOR ANTIBIOTICS | STREPTOMYCES SP | SITE MODELS | PYRINDAMYCIN-A | ANALOGS | ENT-(-)-DUOCARMYCIN SA | BINDING SUBUNIT | CHEMISTRY, ORGANIC | VINYL-CHLORIDE | LINKING AMIDE | Molecular Conformation | Oligodeoxyribonucleotides - chemistry | Models, Molecular | Crystallography, X-Ray | Alkylation | Alkylating Agents - chemistry | DNA, Viral - chemistry | DNA - chemistry | Quinolones - chemistry | Antibiotics, Antineoplastic - chemistry | Quinolones - chemical synthesis | Base Sequence | Pyrroles - chemistry | Indicators and Reagents | Molecular Structure | Indoles | Leucomycins - chemistry | Indolequinones | Research | Catalysis | Alkylating agents | Analysis | Structure-activity relationships (Biochemistry)
Journal Article
Chemical science, ISSN 2041-6520, 10/2016, Volume 7, Issue 10, pp. 6407 - 6412
A photoredox-mediated Minisci C-H alkylation reaction of -heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl...
Journal Article
Chemical Science, ISSN 2041-6520, 2014, Volume 5, Issue 7, pp. 2893 - 2898
Sunlight-induced direct regioselective beta-alkylation of cyclopentanones with electron-deficient alkenes was accomplished by using tetrabutylammonium...
FUNCTIONALIZATION | CYCLIC-KETONES | CATALYSIS | ALKENES | PHOTOREDOX | ARYLATION | PEROXYCARBONATE | ARYL KETONES | CHEMISTRY, MULTIDISCIPLINARY | C-H BONDS | RADICAL REACTIONS | Sunlight | Alkenes | Catalysts | Acylation
FUNCTIONALIZATION | CYCLIC-KETONES | CATALYSIS | ALKENES | PHOTOREDOX | ARYLATION | PEROXYCARBONATE | ARYL KETONES | CHEMISTRY, MULTIDISCIPLINARY | C-H BONDS | RADICAL REACTIONS | Sunlight | Alkenes | Catalysts | Acylation
Journal Article