Copper-mediated oxidative C−H/N−H activations with alkynes by removable hydrazides

• Feng Xiong,
• Bo Li,
• Chenrui Yang,
• Liang Zou,
• Wenbo Ma,
• Linghui Gu,
• Ruhuai Mei and
• Lutz Ackermann

Beilstein J. Org. Chem. 2021, 17, 1591–1599, doi:10.3762/bjoc.17.113

• -pyridylhydrazide allowed for domino C–H/N–H functionalization. The approach featured remarkable functional group compatibility and ample substrate scope. Thereby, highly functionalized aromatic and heteroaromatic isoindolin-1-ones were accessed with high efficacy with rate-limiting C–H cleavage. Keywords

• -catalyzed C−H activations with the MHP auxiliary [41][42][43][44]. In continuation of studies on sustainable 3d transition metal-catalyzed C−H activation [41][42][43][44][45][46][47][48][49], we have now discovered a robust copper-promoted oxidative C−H/N−H functionalization with terminal alkynes (Figure 1d

• C−H/N−H activation. Copper-mediated oxidative C−H/N−H functionalization of hydrazides 1 with ethynylbenzene (2a). Copper-mediated oxidative C−H/N−H functionalization of 1 with alkynes 2. Decaboxylative C−H/N−H activation and cleavage of the directing group. Summary of key mechanistic findings

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

• Gianluigi Broggini,
• Egle M. Beccalli,
• Andrea Fasana and
• Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

• 10.3762/bjoc.8.198 Abstract This review highlights the development of palladium-catalyzed C–H and N–H functionalization reactions involving indole derivatives. These procedures require unactivated starting materials and are respectful of the basic principle of sustainable chemistry tied to atom economy

• . Keywords: alkenylation; arylation; C–H functionalization; indoles; N–H functionalization; Pd catalysis; Introduction The development of mild and selective reactions for the direct conversion of carbon–hydrogen bonds into carbon–carbon and carbon–heteroatom bonds is a challenging goal in organic chemistry

• . This N-(2-pyridyl)sulfonyl-directing strategy has also been extended to the development of a protocol for the intermolecular, dehydrogenative homocoupling of indole, providing 2,2’-bisindoles 7. Intermolecular Pd(II)-catalyzed N–H functionalization has also been successfully used to achieve N