Palladium-Catalyzed Unactivated C(sp³)–H Bond Activation and Intramolecular Amination of Carboxamides: A New Approach to β‑Lactams

An efficient method to synthesize the β-lactams with high regioselectivity via Pd-catalyzed C­(sp³)–H bond activation and intramolecular amination of simple and readily available aminoquinoline carboxamides was demonstrated. C₆F₅I plays a significant role in the formation of the C–N bond of the four-membered ring β-lactams. High yield along with wide substrate scope and functional group tolerance makes this reaction applicable to build natural-product-derived β-lactams. This method has been applied to the efficient synthesis of the β-lactamase inhibitor MK-8712

Palladium-Catalyzed Unactivated C(sp³)–H Bond Activation and Intramolecular Amination of Carboxamides: A New Approach to β‑Lactams

An efficient method to synthesize the β-lactams with high regioselectivity via Pd-catalyzed C­(sp³)–H bond activation and intramolecular amination of simple and readily available aminoquinoline carboxamides was demonstrated. C₆F₅I plays a significant role in the formation of the C–N bond of the four-membered ring β-lactams. High yield along with wide substrate scope and functional group tolerance makes this reaction applicable to build natural-product-derived β-lactams. This method has been applied to the efficient synthesis of the β-lactamase inhibitor MK-8712

Palladium-Catalyzed Unactivated C(sp³)–H Bond Activation and Intramolecular Amination of Carboxamides: A New Approach to β‑Lactams

An efficient method to synthesize the β-lactams with high regioselectivity via Pd-catalyzed C­(sp³)–H bond activation and intramolecular amination of simple and readily available aminoquinoline carboxamides was demonstrated. C₆F₅I plays a significant role in the formation of the C–N bond of the four-membered ring β-lactams. High yield along with wide substrate scope and functional group tolerance makes this reaction applicable to build natural-product-derived β-lactams. This method has been applied to the efficient synthesis of the β-lactamase inhibitor MK-8712

Palladium-Catalyzed Unactivated C(sp³)–H Bond Activation and Intramolecular Amination of Carboxamides: A New Approach to β‑Lactams

An efficient method to synthesize the β-lactams with high regioselectivity via Pd-catalyzed C­(sp³)–H bond activation and intramolecular amination of simple and readily available aminoquinoline carboxamides was demonstrated. C₆F₅I plays a significant role in the formation of the C–N bond of the four-membered ring β-lactams. High yield along with wide substrate scope and functional group tolerance makes this reaction applicable to build natural-product-derived β-lactams. This method has been applied to the efficient synthesis of the β-lactamase inhibitor MK-8712

Stereoselective Synthesis of Diazabicyclic β‑Lactams through Intramolecular Amination of Unactivated C(sp³)–H Bonds of Carboxamides by Palladium Catalysis

An efficient C­(sp³)–H bond activation and intramolecular amination reaction via palladium catalysis at the β-position of carboxyamides to make β-lactams was described. The investigation of the substrate scope showed that the current reaction conditions favored activation of the β-methylene group. Short sequences were developed for preparation of various diazabicyclic β-lactam compounds with this method as the key step from chiral proline and piperidine derivatives

Metal-Free Regioselective Hypervalent Iodine-Mediated C‑2 and C‑3 Difunctionalization of <i>N</i>‑Substituted Indoles

Mild, metal-free, highly regioselective hypervalent-iodine mediated C-2 acetoxylation and C-3 oxidations of <i>N</i>-substituted indoles with (diacetoxyiodo)­benzene [PhI­(OAc)₂] have been reported. The reaction involves three cascade steps. The quantity of PhI­(OAc)₂ employed in this reaction plays a key role in the outcome of three types of products (<b>2a</b>–<b>4a</b>). Furthermore, the mild and highly regioselective C-2 oxidation and C-3 dichlorination of <i>N</i>-substituted indoles with PhICl₂ have been developed. Extensive studies including in situ IR techniques and H₂O¹⁸-labeling experiment were performed to gain insight into the possible reaction mechanism

Metal-Free Regioselective Hypervalent Iodine-Mediated C‑2 and C‑3 Difunctionalization of <i>N</i>‑Substituted Indoles

Mild, metal-free, highly regioselective hypervalent-iodine mediated C-2 acetoxylation and C-3 oxidations of <i>N</i>-substituted indoles with (diacetoxyiodo)­benzene [PhI­(OAc)₂] have been reported. The reaction involves three cascade steps. The quantity of PhI­(OAc)₂ employed in this reaction plays a key role in the outcome of three types of products (<b>2a</b>–<b>4a</b>). Furthermore, the mild and highly regioselective C-2 oxidation and C-3 dichlorination of <i>N</i>-substituted indoles with PhICl₂ have been developed. Extensive studies including in situ IR techniques and H₂O¹⁸-labeling experiment were performed to gain insight into the possible reaction mechanism