Cobalt-Catalyzed Synthesis of Alkenyl Heterocycles via Regioselective Intramolecular 1,4-Hydrofunctionalization of Dienes

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 25, 2024

We report a novel cobalt-catalyzed intramolecular 1,4-hydrofunctionalization of dienes. The reaction proceeds under mild conditions and is amenable to N- O-nucleophiles. protocol exhibits exclusive regioselectivity, yielding number different alkenyl heterocycles, including but not limited dihydroisobenzofurans, isochromanes, tetrahydrofurans, morpholines, lactones, isoindolines. Experimental studies were performed offer some insight into the mechanistic pathways rationalize regio- stereoselectivities reaction.

Language: Английский

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Rhodium-Catalyzed Annulation of Vinylated Tyrosines with Internal Alkynes to Access Oxepine-Mounted Unnatural Tyrosines and Its Peptide Late Stage Functionalization

Organic Letters, Journal Year: 2022, Volume and Issue: 24(37), P. 6857 - 6862

Published: Sept. 8, 2022

A Rh(III)-catalyzed [5+2] annulation of vinyl tyrosines with symmetrical and unsymmetrical internal alkynes was achieved, furnishing a series oxepine-mounted tyrosine-based unnatural amino acids. In addition, the chemical applicability developed strategy exemplified by stapling acid/peptide-appended late stage functionalization tyrosine-containing dipeptides tripeptide alkynes.

Language: Английский

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Rhodium(III)-Catalyzed Sequential Cyclization of Enaminones with 1,3-Dienes via C–H Activation for the Synthesis of Fluorenones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 19, 2024

An efficient method for construction of various fluorenones has been achieved via Rh(III)-catalyzed C–H activation/[4 + 2] annulation/aromatization sequences simple and readily available enaminones 1,3-dienes. This protocol showed good substrate compatibility as an array structurally electronically diverse prepared efficiently in moderate to yields preparative scale utility showing very efficiency the late-stage functionalization complex valuable molecules.

Language: Английский

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Rh(iii)-Catalyzed chemo-, regio- and stereoselective carboamination of sulfonyl allenes with N-phenoxy amides or N-enoxy imides

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(66), P. 9286 - 9289

Published: Jan. 1, 2022

The Rh(III)-catalyzed chemo-, regio- and stereoselective carboamination of sulfonyl allenes has been realized by virtue either N-phenoxy amides or N-enoxy imides simultaneously acting as the C- N-sources, via redox-neutral tandem C-H activation/allene insertion/oxidative addition/C-N bond formation for direct construction allylamine derivatives equipped with an α-quaternary carbon center. This protocol features high atom-economy good substrate compatibility exhibits profound synthetic potential late-stage modification complex molecules.

Language: Английский

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Copper‐Catalyzed Intramolecular S_EAr Reaction–Oxidation under Aerobic Conditions: Synthesis of Styryl‐/Alkenyl‐Substituted Xanthone Derivatives

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(23)

Published: April 29, 2023

Abstract Herein, we report a copper‐catalyzed intramolecular electrophilic aromatic substitution (S E Ar)−oxidation process to access wide range of diversified xanthone derivatives using air as sole oxidant. Specifically, this protocol affords hitherto unknown styryl‐/alkenyl‐substituted in moderate high yields. The practicality the method has been demonstrated by gram‐scale syntheses.

Language: Английский

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Rhodium(III)‐Catalyzed Cascade C−H Coupling/C‐Terminus Michael Addition of N‐Phenoxy Amides with 1,6‐Enynes

ChemistrySelect, Journal Year: 2021, Volume and Issue: 6(25), P. 6574 - 6578

Published: July 1, 2021

Abstract Described herein is a Rh(III)‐catalyzed regio‐/stereoselective C−H coupling/C‐terminus Michael addition cascade of N ‐phenoxy amides with 1,6‐enynes, giving access to bicyclic frameworks the retention oxidizing directing groups. Thus, it also provides straightforward platform for subsequent derivatization via two‐fold functionalization. Mechanistic studies elucidate tandem reaction path and coordination effect in tuning observed manifold.

Language: Английский

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Redox-neutral rhodium(iii)-catalyzed divergent synthesis of tetrasubstituted 1,3-enynes and alkynylated benzofurans

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(1), P. 147 - 152

Published: Nov. 28, 2022

With the assistance of acetamido directing group (DG), a rhodium-catalyzed C-H alkenylation/DG migration cascade for synthesis tetrasubstituted 1,3-enynes from N-phenoxyacetamides and 1,3-diynes has been achieved in this work. Alternatively, [3 + 2] annulation alkynylated benzofurans same set substrates also by simply changing reaction conditions. This work highlights tunable divergent valuable compounds triggered activation.

Language: Английский

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Rh(III)-Catalyzed Tandem [4+2] Annulation To Construct Functional Dihydroisoquinolinones

Synthesis, Journal Year: 2022, Volume and Issue: 54(14), P. 3271 - 3281

Published: March 3, 2022

Abstract A highly efficient Rh(III)-catalyzed tandem [4+2] annulation to construct functional dihydroisoquinolinone derivatives with an alkenyl side chain by insertion into N–O bond as internal oxidation process has been achieved. wide range of 1,3-dienes the coupling partners makes this simple methodology even more useful.

Language: Английский

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