Iridium‐Catalyzed β‐Alkynylation of Aliphatic Oximes as Masked Carbonyl Compounds and Alcohols

Alkynylation reactions are one of the most sought‐after synthetic methodologies due to the versatility of C−C triple bond diversifications. Sonogashira coupling was widely used for the synthesis of alkynylated molecules; however, this methodology requires the use of previously halogenated substrates, which is a major drawback. To overcome this issue, a complimentary method, transition‐metal‐catalyzed C−H alkynylation, was emerged as an alternative tool in the recent years. Though the initial reports required the use of either specific directing groups or strong alkynylating agents for effective functionalization, recent studies indicate that transition‐metal‐catalyzed site selective alkynylations can be carried out using mild and readily available alkynylating agents under moderate reaction conditions. In this review, we explain the transition metal cataluyzed site selective alkynylation both C(sp2)−H and C(sp3)−H bonds by emphasizing to the reaction mechanism.

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Transition‐Metal‐Catalyzed Selective Alkynylation of C−H Bonds

Sarala

Bhowmick

Carvalho

et al. 2021

Adv Synth Catal

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Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp³)−H Bonds

et al. 2022

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C(sp 3 )À H functionalization is a core part of organic chemistry because of the presence of C(sp 3 )À H bonds in various organic molecules. However, since most C(sp 3 )À H bonds are non-reactive, their functionalization is an uphill task. Standard methods of functionalization employ prefunctionalized reactants, expensive organometallic reagents, strong acids or bases and similar other harsh reaction conditions. These methods eventually affect the reaction and prevent it from yielding optimum results. Transition metalbased catalysts like Pd, Rh and Ru provide a direct functionalization route without unwanted pre-functionalization steps. These catalysts furnish superior results under mild reaction conditions. But, their expense, toxicity and low natural abundance prevent them from achieving ideality. Therefore, 3d transition metal catalysts like Mn, Fe, Co, Ni and Cu catalysts have gained significance as an alternative for conventional transition metal catalysts due to their high natural abundance, low toxicity and affordability. Copperbased catalysts are particularly important owing to the wide range of oxidation states of copper and the facile tunability of their catalytic properties. Hence, an immense amount of research is being conducted on the catalytic activity of copper for C(sp 3 )À H functionalization. This review aims to provide a detailed overview of some recent reports on C(sp 3 )À H functionalization using catalytic systems based on copper.

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Rhodium(III)‐Catalyzed Synthesis of Skipped Enynes via C(sp³)–H Alkynylation of Terminal Alkenes

et al. 2021

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The RhIII‐catalyzed allylic C−H alkynylation of non‐activated terminal alkenes leads selectively to linear 1,4‐enynes at room‐temperature. The catalytic system tolerates a wide range of functional groups without competing functionalization at other positions. Similarly, the vinylic C−H alkynylation of α,β‐ and β,γ‐ unsaturated amides gives conjugated Z‐1,3‐enynes and E‐enediynes.

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Iridium‐Catalyzed β‐Alkynylation of Aliphatic Oximes as Masked Carbonyl Compounds and Alcohols

Cited by 8 publications

References 54 publications

Transition‐Metal‐Catalyzed Selective Alkynylation of C−H Bonds

Transition‐Metal‐Catalyzed Selective Alkynylation of C−H Bonds

Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp³)−H Bonds

Rhodium(III)‐Catalyzed Synthesis of Skipped Enynes via C(sp³)–H Alkynylation of Terminal Alkenes

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Iridium‐Catalyzed β‐Alkynylation of Aliphatic Oximes as Masked Carbonyl Compounds and Alcohols

Cited by 8 publications

References 54 publications

Transition‐Metal‐Catalyzed Selective Alkynylation of C−H Bonds

Transition‐Metal‐Catalyzed Selective Alkynylation of C−H Bonds

Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp3)−H Bonds

Rhodium(III)‐Catalyzed Synthesis of Skipped Enynes via C(sp3)–H Alkynylation of Terminal Alkenes

Contact Info

Product

Resources

About

Recent Advances in Copper‐Catalyzed Functionalization of Unactivated C(sp³)−H Bonds

Rhodium(III)‐Catalyzed Synthesis of Skipped Enynes via C(sp³)–H Alkynylation of Terminal Alkenes