Recent Applications of Rh‐ and Pd‐Catalyzed C(sp3)–H Functionalization in Natural Product Total Synthesis
Sign Up to like & getrecommendations! Published in 2017 at "European Journal of Organic Chemistry"
DOI: 10.1002/ejoc.201700641
Abstract: The advent of C(sp3)–H functionalization has heralded a paradigm shift in natural product synthesis. Indeed, several reports in which C–H functionalization serves as the key step in the synthesis have appeared over the years. The… read more here.
Keywords: sp3 functionalization; catalyzed sp3; total synthesis; natural product ... See more keywords
Direct C(sp3)-H functionalization of 2-methylazaarenes using 4-substituted-TEMPO
Sign Up to like & getrecommendations! Published in 2018 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2018.10.014
Abstract: Abstract An efficient and direct C(sp3)-H functionalization of 2-methyl azaarenes with persistent nitroxide radical 4-substituted-2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) under neutral conditions has been developed. A broad of 2-methylazaarenes could be reacted with 4-substituted TEMPOs to afford corresponding… read more here.
Keywords: methylazaarenes using; sp3 functionalization; direct sp3; using substituted ... See more keywords
Copper-Catalyzed, N-Directed Distal C(sp3)-H Functionalization toward Azepanes.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c03135
Abstract: We herein report a copper-catalyzed formal [5 + 2] aza-annulation of N-fluorosulfonamides and 1,3-dienes/1,3-enynes for synthesis of structurally diverse alkene/alkyne-containing azepanes. The reaction features selective functionalization of distal unactivated C(sp3)-H bonds and a broad substrate… read more here.
Keywords: distal sp3; catalyzed directed; directed distal; sp3 functionalization ... See more keywords
Palladium-Catalyzed Redox-Neutral N-O/C(sp3)-H Functionalization of Aryl Oximes with Isocyanides.
Sign Up to like & getrecommendations! Published in 2017 at "Organic letters"
DOI: 10.1021/acs.orglett.6b03852
Abstract: A redox-neutral palladium-catalyzed N-O/C(sp3)-H functionalization of aryl oximes with isocyanides has been developed. Various pyrrole derivatives were prepared in good to excellent yields through oxime carbamate as a key intermediate and internal oxidant in this… read more here.
Keywords: sp3 functionalization; functionalization aryl; redox neutral; palladium catalyzed ... See more keywords
Copper-Catalyzed Intermolecular [4 + 2] Annulation Enabled by Internal Oxidant-Promoted C(sp3)-H Functionalization: Access to 3-Trifluoromethylated 3-Hydroxy-cyclohexan-1-ones.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b01817
Abstract: A copper-catalyzed diastereoselective [4 + 2] cyclolization of α,β-unsaturated ketoxime acetates and trifluoromethyl ketones affords various 3-trifluoromethylated 3-hydroxy-cylcohexan-1-ones smoothly. This reaction features the selective functionalization of a less acidic C(sp3)-H bond by an internal oxdative… read more here.
Keywords: catalyzed intermolecular; trifluoromethylated hydroxy; sp3 functionalization; internal oxidant ... See more keywords
Catalyst- and Additive-Free C(sp3)–H Functionalization of (Thio)barbituric Acids via C-5 Dehydrogenative Aza-Coupling Under Ambient Conditions
Sign Up to like & getrecommendations! Published in 2022 at "ACS Omega"
DOI: 10.1021/acsomega.2c03073
Abstract: A one-pot room-temperature-based three-component reaction strategy has been accomplished to access a new series of bio-relevant barbituric/2-thiobarbituric acid hydrazones from the reaction between barbituric/2-thiobarbituric acids, primary aromatic amines, and tert-butyl nitrite in an acetonitrile solvent,… read more here.
Keywords: via dehydrogenative; sp3 functionalization; reaction; acids via ... See more keywords
Choline Chloride-Based Deep Eutectic Systems in Sequential Friedländer Reaction and Palladium-Catalyzed sp3 CH Functionalization of Methyl Ketones
Sign Up to like & getrecommendations! Published in 2019 at "ACS Omega"
DOI: 10.1021/acsomega.9b00310
Abstract: A volatile organic solvent-free and choline chloride (ChCl)-based deep eutectic system (DES)-mediated sp3-CH functionalization of acetophenones 1 with benzyl alcohols 2 to the corresponding α, β-saturated ketones 3 is accounted for. The domino dehydrogenation–aldol condensation… read more here.
Keywords: sp3 functionalization; functionalization; deep eutectic; based deep ... See more keywords
Enantioselective C(sp3)-H Functionalization of Oxacycles via Photo-HAT/Nickel Dual Catalysis.
Sign Up to like & getrecommendations! Published in 2023 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c12481
Abstract: The selective functionalization of ubiquitous but inert C-H bonds is highly appealing in synthetic chemistry, but the direct transformation of hydrocarbons lacking directing groups into high-value chiral molecules remains a formidable challenge. Herein, we develop… read more here.
Keywords: sp3 functionalization; functionalization; enantioselective sp3; via photo ... See more keywords
Chiral phosphoric acid-catalyzed asymmetric C(sp3)–H functionalization of biomass-derived 2,5-dimethylfuran via two sequential Cope-type rearrangements
Sign Up to like & getrecommendations! Published in 2019 at "Organic Chemistry Frontiers"
DOI: 10.1039/c8qo01375f
Abstract: The first organocatalytic asymmetric C(sp3)–H functionalization of biomass-derived 2,5-dimethylfuran with alcohols to afford enantioenriched furan-derived 3,3′-disubstituted oxindoles in high enantioselectivity. read more here.
Keywords: derived dimethylfuran; sp3 functionalization; functionalization biomass; biomass derived ... See more keywords
Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis.
Sign Up to like & getrecommendations! Published in 2019 at "Chemical communications"
DOI: 10.1039/c9cc04287c
Abstract: A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram… read more here.
Keywords: sp3 functionalization; enabled visible; heterocyclization involving; functionalization enabled ... See more keywords
Metal-free C(sp3)–H functionalization of sulfonamides via strain-release rearrangement†
Sign Up to like & getrecommendations! Published in 2021 at "Chemical Science"
DOI: 10.1039/d0sc06603f
Abstract: With the increasing awareness of sustainable chemistry principles, the development of an efficient and mild strategy for C(sp3)–H bond activation of nitrogen-containing compounds without the utilization of any oxidant and metal is still highly desired… read more here.
Keywords: sp3 functionalization; free sp3; metal; metal free ... See more keywords