Dual C(sp³)−H Bond Functionalization of N‐Heterocycles through Sequential Visible‐Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions

Abstract

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Visible Light‐induced Functionalization of C−H Bonds: Opening of New Avenues in Organic Synthesis

“…A novel method for dual C(sp 3 )−H functionalization of saturated nitrogenous heterocycles ( 64 ) was disclosed by Xu and coworkers with ruthenium photocatalyst [65] . Sequential dehydrogenation/[2+2] cycloaddition process first generated a highly reactive enamine intermediate from saturated heterocycles under photocatalytic conditions.…”

“…A novel method for dual C(sp 3 )À H functionalization of saturated nitrogenous heterocycles (64) was disclosed by Xu and coworkers with ruthenium photocatalyst. [65] Sequential dehydrogenation/[2 + 2] cycloaddition process first generated a highly reactive enamine intermediate from saturated heterocycles under photocatalytic conditions. The enamine intermediate so generated then coupled with acetylene esters (65) via [2 + 2] cycloaddition reaction to furnish desired bicyclic amino acids derivatives (66) in good to excellent yields (Scheme 25).…”

Synthesis of the Hexahydropyrrolo-[3,2-c]-quinoline Core Structure and Strategies for Further Elaboration to Martinelline, Martinellic Acid, Incargranine B, and Seneciobipyrrolidine

“…Instead, he proposed that dimerization occurred between a pyrrolocarbene, formed from α-elimination of dimethyl phenyl silane oxide, and the corresponding dimethyl phenyl silane enolate. Formation of the dipyrroloquinoline 241 as a side product dimer when utilizing N -phenyl pyrrolidine in reactions with oxidative conditions is today a well-known issue [ 106 , 107 , 108 , 109 , 110 , 111 , 112 ].…”

Metal-free C(sp3)–H functionalization of sulfonamidesviastrain-release rearrangement

“… 3 Given the medicinal value of β-substituted amine derivatives, 4 some methods for β-C–H functionalization have been developed based on an oxidative cross-coupling pathway ( Scheme 1A ). 5,6 These reactions often require transition metals (Ru, Ir, Pd and Fe), 7–10 oxidizing reagents 11 and high temperature. 12 In contrast, transition metal-free protocols are very rare in this field.…”