Aerobic iron-catalyzed site-selective C(sp3)–C(sp3) bond cleavage in N-heterocycles
Sign Up to like & getrecommendations! Published in 2021 at "Catalysis Communications"
DOI: 10.1016/j.catcom.2021.106333
Abstract: Abstract The kinetic and thermodynamic stability of C(sp3)–C(sp3) bonds makes the site-selective activation of these motifs a real synthetic challenge. In view of this, herein a site-selective method of C(sp3)–C(sp3) bond scission of amines, specifically… read more here.
Keywords: sp3 sp3; sp3; site selective; sp3 bond ... See more keywords
Recent advances on iron-catalyzed coupling reactions involving organolithium reagents
Sign Up to like & getrecommendations! Published in 2019 at "Chinese Chemical Letters"
DOI: 10.1016/j.cclet.2019.05.026
Abstract: Abstract Owing to their inexpensive and environmentally friendly properties, iron-based catalysts have been actively investigated for new organic reactions. In this account, we summarized our recent results on iron-catalyzed cross-coupling reactions and homo-coupling reactions. With… read more here.
Keywords: iron catalyzed; catalyzed coupling; sp3 sp3; recent advances ... See more keywords
Nickel-Catalyzed C(sp3)-C(sp3) Cross-Electrophile Coupling of In Situ Generated NHP Esters with Unactivated Alkyl Bromides.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00805
Abstract: The formation of C(sp3)-C(sp3) bonds by cross-coupling remains a challenge in synthesis. Here, we demonstrate a two-step, one-pot protocol for the in situ generation of N-hydroxyphthalimide esters and their nickel-catalyzed cross-electrophile coupling with unactivated alkyl… read more here.
Keywords: unactivated alkyl; nickel catalyzed; sp3; sp3 sp3 ... See more keywords
C(sp3)-H/C(sp3)-H Dehydrogenative Radical Coupling of Glycine Derivatives.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c02951
Abstract: Here we report a general C(sp3)-H/C(sp3)-H dehydrogenative coupling strategy for the preparation of various natural or unnatural amino acids from readily available glycine derivatives and hydrocarbons through a combination of SET and HAT process. read more here.
Keywords: sp3 dehydrogenative; sp3 sp3; glycine derivatives; radical coupling ... See more keywords
Preparation of Alkyl Di(p-tolyl)sulfonium Salts and Their Application in Metal-Free C(sp3)-C(sp3) and C(sp3)-C(sp2) Bond Formations.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c01233
Abstract: Alkyldiarylsulfonium salts were synthesized by a combination of active sulfonium species, prepared through the activation of diarylsulfoxide, and alkyl nucleophiles. The isolated sulfonium salts were subjected to the allylation and cyclopropanation of the active methylene… read more here.
Keywords: metal free; sp3; sp3 sp3; free sp3 ... See more keywords
Fully Automated Flow Protocol for C(sp3)-C(sp3) Bond Formation from Tertiary Amides and Alkyl Halides.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c01390
Abstract: Herein, we present a novel C(sp3)-C(sp3) bond-forming protocol via the reductive coupling of abundant tertiary amides with organozinc reagents prepared in situ from their corresponding alkyl halides. Using a multistep fully automated flow protocol, this… read more here.
Keywords: fully automated; sp3 bond; alkyl halides; sp3 sp3 ... See more keywords
Nontraditional Fragment Couplings of Alcohols and Carboxylic Acids: C(sp3)-C(sp3) Cross-Coupling via Radical Sorting.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c02062
Abstract: Alcohols and carboxylic acids are among the most commercially abundant, synthetically versatile, and operationally convenient functional groups in organic chemistry. Under visible light photoredox catalysis, these native synthetic handles readily undergo radical activation, and the… read more here.
Keywords: alcohols carboxylic; cross coupling; sp3 sp3; sp3 cross ... See more keywords
Ni/Photoredox-Catalyzed C(sp3)-C(sp3) Coupling between Aziridines and Acetals as Alcohol-Derived Alkyl Radical Precursors.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c09294
Abstract: Aziridines are readily available C(sp3) precursors that afford valuable β-functionalized amines upon ring opening. In this article, we report a Ni/photoredox methodology for C(sp3)-C(sp3) cross-coupling between aziridines and methyl/1°/2° aliphatic alcohols activated as benzaldehyde dialkyl… read more here.
Keywords: cross coupling; sp3; coupling aziridines; sp3 sp3 ... See more keywords
Enantioselective C(sp3)-C(sp3) Reductive Cross-Electrophile Coupling of Unactivated Alkyl Halides with α-Chloroboronates via Dual Nickel/Photoredox Catalysis.
Sign Up to like & getrecommendations! Published in 2023 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c13220
Abstract: Substantial advances in enantioconvergent C(sp3)-C(sp3) bond formations have been made with nickel-catalyzed cross-coupling of racemic alkyl electrophiles with organometallic reagents or nickel-hydride-catalyzed hydrocarbonation of alkenes. Herein, we report an unprecedented enantioselective C(sp3)-C(sp3) reductive cross-coupling by… read more here.
Keywords: sp3 reductive; sp3; enantioselective sp3; sp3 sp3 ... See more keywords
Photo-Uncaging by C(sp3)-C(sp3) Bond Cleavage Restores β-Lapachone Activity.
Sign Up to like & getrecommendations! Published in 2023 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.3c00398
Abstract: β-Lapachone is an ortho-naphthoquinone natural product with significant antiproliferative activity but suffers from adverse systemic toxicity. The use of photoremovable protecting groups to covalently inactivate a substrate and then enable controllable release with light in… read more here.
Keywords: cleavage; sp3 bond; sp3 sp3; activity ... See more keywords
Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp3)-C(sp3)/C(sp3)-C(sp2) Bond Formation and Mechanistic Studies.
Sign Up to like & getrecommendations! Published in 2018 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.8b05374
Abstract: We report a Ni-catalyzed regioselective alkylarylation of vinylarenes with alkyl halides and arylzinc reagents to generate 1,1-diarylalkanes. The reaction proceeds well with primary, secondary and tertiary alkyl halides, and electronically diverse arylzinc reagents. Mechanistic investigations… read more here.
Keywords: sp3; regioselective alkylarylation; alkylarylation vinylarenes; catalyzed regioselective ... See more keywords