Direct C(sp2)−H Hydroxylation of Arenes with Palladium(II)/Oxygen Using Sulfoximines as a Recyclable Directing Group
Sign Up to like & getrecommendations! Published in 2018 at "ChemCatChem"
DOI: 10.1002/cctc.201800064
Abstract: The aerobic palladium(II) catalysis presented herein offers facile entry to various substituted phenols through site‐selective C−H hydroxylation of arenes by using sulfoximines as a reusable directing group. The notable aspects of our method include the… read more here.
Keywords: oxygen; directing group; hydroxylation; palladium ... See more keywords
Switchable C−H Alkylation of Aromatic Acids with Maleimides in Water: Carboxyl as a Diverse Directing Group
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DOI: 10.1002/cctc.201900444
Abstract: A ruthenium‐catalyzed protocol to access conjugate addition or decarboxylative conjugate addition of aromatic acids with maleimides has been developed. The reaction shows interesting chemoselectivity with different substituted benzoic acids. The reaction pathway of C−H alkylation… read more here.
Keywords: addition; directing group; aromatic acids; group ... See more keywords
Emergence of Pyrimidine-Based meta-Directing Group: Journey from Weak to Strong Coordination in Diversifying meta-C-H Functionalization.
Sign Up to like & getrecommendations! Published in 2022 at "Accounts of chemical research"
DOI: 10.1021/acs.accounts.1c00629
Abstract: ConspectusC-H activation has emerged as a powerful transformative synthetic tool to construct complex molecular frameworks, which are ubiquitous in natural products, medicines, dyes, polymers, and many more. However, reactivity and selectivity, arising from the inertness… read more here.
Keywords: meta; meta functionalization; directing group; activation ... See more keywords
Directing Group Guided Site-Selective Diversification of Indoles by Aziridine: Synthesis of β-Indolylethylamines.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00120
Abstract: A palladium catalyzed directing group assisted cross-coupling of aliphatic aziridines with indole, indoline, tetrahydroquinoline, and aniline has been developed to furnish the corresponding β-arylethylamine derivatives. The substrate scope was very general, and the protocol was… read more here.
Keywords: guided site; site selective; group; selective diversification ... See more keywords
4-Aminobenzotriazole (ABTA) as a Removable Directing Group for Palladium-Catalyzed Aerobic Oxidative C-H Olefination.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00285
Abstract: 4-Aminobenzotriazole (ABTA) was applied as an effective removable directing group (DG) in Pd-catalyzed C-H activation for the first time. Compared with the widely applied pyridine and quinoline analogs, ABTA showed significantly improved reactivity, achieving aerobic… read more here.
Keywords: aerobic oxidative; aminobenzotriazole abta; removable directing; oxidative olefination ... See more keywords
Pd(II)-Catalyzed Transient Directing Group-Assisted Regioselective Diverse C4-H Functionalizations of Indoles.
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DOI: 10.1021/acs.orglett.2c00320
Abstract: The development of a rational strategy for achieving site-selective C4-H halogenation of indoles is an appealing yet challenging task. Herein, we disclose a Pd(II)-catalyzed transient directing group (TDG)-assisted methodology for realizing C4 chlorination/bromination of indoles… read more here.
Keywords: transient directing; methodology; group assisted; catalyzed transient ... See more keywords
Triazene as the Directing Group Achieving Highly Ortho-Selective Diborylation and Sequential Functionalization.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c00994
Abstract: This study describes a regioselective ortho,ortho'-diborylation of aromatic triazenes catalyzed by [Ir(OMe)(cod)]2 in near-quantitative yields without an additional ligand. Aromatic triazenes act as both substrates and ligands. The X-ray structures of 2a and 2p indicate… read more here.
Keywords: group achieving; diborylation; triazene directing; achieving highly ... See more keywords
Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines.
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DOI: 10.1021/acs.orglett.7b00715
Abstract: A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and… read more here.
Keywords: directing group; anilines allyl; traceless directing; allyl alcohols ... See more keywords
Dual Role of Anthranils as Amination and Transient Directing Group Sources: Synthesis of 2-Acyl Acridines.
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DOI: 10.1021/acs.orglett.8b01571
Abstract: The transient directing group promoted C(sp2)-H functionalization of benzaldehydes with anthranils by a cationic rhodium(III) catalyst is described. Notably, anthranils have been used as both transient directing groups and amination sources to afford 2-acyl acridines… read more here.
Keywords: acyl acridines; dual role; directing group; group ... See more keywords
Palladium-Catalyzed β-C-H Arylation of Aliphatic Aldehydes and Ketones Using Amino Amide as a Transient Directing Group.
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DOI: 10.1021/acs.orglett.9b00366
Abstract: This paper describes a new amino-amide-based transient directing group (TDG). The TDG can exhibit better performance in the Pd-catalyzed arylation of aliphatic aldehydes and ketones. This reaction showed good substrate compatibility and regioselectivity. The results… read more here.
Keywords: aliphatic aldehydes; directing group; arylation aliphatic; amino amide ... See more keywords
Synthesis of Naphthols by Rh(III)-Catalyzed Domino C-H Activation, Annulation, and Lactonization Using Sulfoxonium Ylide as a Traceless Directing Group.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b03182
Abstract: Sulfoxonium ylide directed C-H activation catalyzed by the Rh(III)-catalyst has been disclosed. In this study, sulfoxonium ylide functions as a traceless directing group, which reacts with an unsymmetrical alkyne, 4-hydroxy-2-alkynoate, to form the corresponding furanone-fused… read more here.
Keywords: traceless directing; sulfoxonium ylide; activation; directing group ... See more keywords