Ni-catalyzed unnatural prenylation and cyclic monoterpenation of heteroarenes with isoprene

Zhang, Gong; Zhang, Wei‐Song; Wang, X.-Z.; Yang, Yongrong; Ji, Ding‐Wei; Wan, Boshun

doi:10.1016/s1872-2067(23)64437-7

Cited by 2 publications

(4 citation statements)

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“…Given its characteristic structure and abundance, isoprene is undoubtedly the most cost-effective choice for biomimetic constructions of terpenoids. In terms of the synthesis of hemiterpenoids, various catalytic systems have been well developed under transition metal catalysis 12 – 35 . Besides, with the regulation of ligand, Beller, Finn, Réau, Navarro, Carbó and our group reported palladium catalyzed nucleophilic telomerization of isoprene to produce acyclic monoterpenoids 32 , 36 – 44 .…”

Section: Introductionmentioning

confidence: 99%

“…With the aid of N -heterocyclic carbene (NHC) ligands, we have recently demonstrated a selective heteroarylative cyclotelomerization of isoprene for the construction of cyclic monoterpenoids (Fig. 1b ) 35 , 46 . Given aromatic compounds play indispensable roles in a broad spectrum of industries, we wonder is it possible to develop a strategy for the creation of aromatic monoterpenoids with a distinctive selectivity.…”

Section: Introductionmentioning

confidence: 99%

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Nucleophilic aromatization of monoterpenes from isoprene under nickel/iodine cascade catalysis

Zhang,

Ji,

Yang

et al. 2023

Nat Commun

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As a large number of organic compounds possessing two isoprene units, monoterpenes and monoterpenoids play important roles in pharmaceutical, cosmetic, agricultural, and food industries. In nature, monoterpenes are constructed from geranyl pyrophosphate (C10) via various transformations. Herein, the bulk C5 chemical—isoprene, is used for the creation of various monoterpenoids via a nucleophilic aromatization of monoterpenes under cascade catalysis of nickel and iodine. Drugs and oil mixtures from conifer and lemon can be convergently transformed to the desired monoterpenoid. Preliminary mechanistic studies are conducted to get insights about reaction pathway. Two types of cyclic monoterpenes can be respectively introduced onto two similar heterocycles via orthogonal C–H functionalization. And various hybrid terpenyl indoles are programmatically assembled from abundant C5 or C10 blocks. This work not only contributes a high chemo-, regio-, and redox-selective transformation of isoprene, but also provides a complementary approach for the creation of unnatural monoterpenoids.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Nucleophilic aromatization of monoterpenes from isoprene under nickel/iodine cascade catalysis

Zhang,

Ji,

Yang

et al. 2023

Nat Commun

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“…5 In contrast, other C 5 isomeric variants, although frequently encountered in bioactive molecules, are rarely synthesized. 6 In view of diversity-oriented synthesis in medicinal chemistry, the synthesis of other C 5 moieties is highly desirable.…”

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confidence: 99%

“…In this regard, the prenylation and reverse prenylation by either enzyme or chemical catalyses have been extensively studied (Figure a) . In contrast, other C 5 isomeric variants, although frequently encountered in bioactive molecules, are rarely synthesized . In view of diversity-oriented synthesis in medicinal chemistry, the synthesis of other C 5 moieties is highly desirable.…”

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confidence: 99%

Palladium-Catalyzed Intermolecular Dehydrogenative C-2 Pentenylation of Indoles with 2-Methyl-2-butene

Zhang,

Wu,

Zhao

et al. 2024

Org. Lett.

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Five-carbon (C 5 ) units are the fundamental building blocks that constitute a multitude of natural products. Herein we report an unprecedented unusual C 5 functionalization of indole regioselectively at the C-2-position enabled by a (2-pyridyl)sulfonyldirecting palladium-catalyzed dehydrogenative strategy with a bulk chemical 2-methyl-2-butene as a C 5 source. Compared to typical C 5 functionalization using pentenyl alcohols, carbonates, borates, or halides as the C 5 source, the protocol not only has a low cost advantage but also is of atom and step economy.

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Ni-catalyzed unnatural prenylation and cyclic monoterpenation of heteroarenes with isoprene

Cited by 2 publications

References 93 publications

Nucleophilic aromatization of monoterpenes from isoprene under nickel/iodine cascade catalysis

Nucleophilic aromatization of monoterpenes from isoprene under nickel/iodine cascade catalysis

Palladium-Catalyzed Intermolecular Dehydrogenative C-2 Pentenylation of Indoles with 2-Methyl-2-butene

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