A Computational Mechanistic Study of Metal‐Catalyzed Remote C–H Functionalizations – Insights into the Origin of Regioselectivity and the Role of Acid
Sign Up to like & getrecommendations! Published in 2017 at "European Journal of Organic Chemistry"
DOI: 10.1002/ejoc.201601111
Abstract: The metal-catalyzed remote C–H functionalization of quinoline N-oxide was investigated systematically through density functional theory calculations. We found that the coordination of the N-oxide moiety to a metal center greatly lowered the barrier to C–H… read more here.
Keywords: quinoline oxide; catalyzed remote; metal; role ... See more keywords
Ag-Catalyzed Remote Unactivated C(sp3)-H Heteroarylation of Free Alcohols in Water.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
DOI: 10.1021/acs.orglett.0c03944
Abstract: Catalyzed by silver salt, the unactivated C(sp3)-H heteroarylation of free alcohol at the δ position is realized under gentle thermal conditions in water through a radical procedure. Both protonic acids and Lewis acids are found… read more here.
Keywords: unactivated sp3; water; catalyzed remote; heteroarylation free ... See more keywords
Palladium-Catalyzed Remote meta-C-H Bond Deuteration of Arenes Using a Pyridine Template.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b01784
Abstract: Palladium-catalyzed meta-selective C-H deuteration of a series of substrates, including phenylacetic acids, hydrocinnamic acid, benzylphosphonate, benzylsulfonate, and benzyl and phenyl ethyl alcohol ester, is developed by using a pyridine-based directing template. The template is installed… read more here.
Keywords: using pyridine; deuteration; template; catalyzed remote ... See more keywords
Palladium-Catalyzed Remote 1,n-Arylamination of Unactivated Terminal Alkenes
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DOI: 10.1021/acscatal.9b00688
Abstract: A palladium-catalyzed remote 1,n-arylamination (from 1,3- to 1,11-arylamination) of unactivated terminal alkenes with aryl iodides and arylamines has been realized. This three-component reaction proceeded via Pd-catalyzed Heck arylation, alkene isomerization, and aza-Michael addition, exhibiting good… read more here.
Keywords: arylamination; catalyzed remote; unactivated terminal; palladium catalyzed ... See more keywords
Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)-H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones.
Sign Up to like & getrecommendations! Published in 2021 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.1c05834
Abstract: A NiH-catalyzed thioether-directed cyclometalation strategy is developed to enable remote methylene C-H bond amidation of unactivated alkenes. Due to the preference for five-membered nickelacycle formation, the chain-walking isomerization initiated by the NiH insertion to an… read more here.
Keywords: directed nih; remote sp3; catalyzed remote; thioether directed ... See more keywords
Nickel-Catalyzed Remote Asymmetric Hydroalkylation of Alkenyl Ethers to Access Ethers of Chiral Dialkyl Carbinols.
Sign Up to like & getrecommendations! Published in 2023 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.3c02950
Abstract: Site- and enantio-selective alkyl-alkyl bond formation is privileged in the retrosynthetic analysis due to the universality of sp3-hybridized carbon atoms in organic molecules. Herein, we report a nickel-catalyzed remote asymmetric hydroalkylation of alkenyl ethers via… read more here.
Keywords: asymmetric hydroalkylation; nickel catalyzed; remote asymmetric; alkenyl ethers ... See more keywords
Nickel-catalyzed remote and proximal Wacker-type oxidation
Sign Up to like & getrecommendations! Published in 2019 at "Communications Chemistry"
DOI: 10.1038/s42004-018-0107-y
Abstract: Wacker oxidation chemistry is widely applied to oxidation of olefins to carbonyls in the synthesis of pharmaceuticals, natural products, and commodity chemicals. However, in this chemistry efficient oxidation of internal olefins and highly selective oxidation… read more here.
Keywords: oxidation; wacker type; catalyzed remote; chemistry ... See more keywords
Transition-metal-catalyzed remote C–H functionalization of thioethers
Sign Up to like & getrecommendations! Published in 2022 at "RSC Advances"
DOI: 10.1039/d2ra01268e
Abstract: In the last decade, transition-metal-catalyzed direct C–H bond functionalization has been recognized as one of most efficient approaches for the derivatization of thioethers. Within this category, both mono- and bidentate-directing group strategies achieved the remote… read more here.
Keywords: transition metal; functionalization; functionalization thioethers; catalyzed remote ... See more keywords
Palladium-catalyzed remote meta-C-H olefination of cinnamates.
Sign Up to like & getrecommendations! Published in 2023 at "Chemical communications"
DOI: 10.1039/d3cc00289f
Abstract: The palladium-catalyzed remote meta-C-H olefination of geometrically challenging substituted cinnamates using a nitrile directing group derived from 2-cyanobenzoic acid has been described. This new protocol is applicable to various olefin coupling partners and provides the… read more here.
Keywords: palladium catalyzed; meta olefination; catalyzed remote; remote meta ... See more keywords