Rhodium(<scp>iii</scp>)-catalyzed unreactive C(sp3)–H alkenylation of N-alkyl-1H-pyrazoles with alkynes

Li, Tongyu; Liu, Chang; Wu, Shaonan; Chen, Chen; Zhu, Bolin

doi:10.1039/c9ob01531k

Cited by 14 publications

(1 citation statement)

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“…Compared to C(sp 2 )–H functionalization, the Cp*Rh(III)-catalyzed direct C(sp 3 )–H bond/functionalization has acquired relatively much less attention, which might be attributed to the challenges of the higher C(sp 3 )–H bond breakage energy and the lower reactivity of generated Rh III –alkyl species. Nevertheless, notable transformations (acylation, alkenylation, alkylation, amination, aminocarbonylation, amidation, trifluoromethylthiolation, etc.) via Rh(III)-catalyzed C(sp 3 )–H activation have been well reported by Li, Kim, Zhao, Lin, Wang, Dixon, Sharma, Lu, and Jiang groups.…”

Section: Introductionmentioning

confidence: 99%

Rh^III–Catalyzed Direct Heteroarylation of Unactivated C(sp³)–H with N-Heteroaryl Boronates

Chi,

Xu,

Liu

et al. 2024

J. Org. Chem.

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Disclosed herein is a rhodium(III)-catalyzed direct heteroarylation reaction between unactivated aliphatic C(sp 3 )−H bonds in 2-alkylpyridines and heteroaryl organoboron reagents. This catalytic protocol is compatible with various heterocyclic boronates containing ortho-and meta-pyridine, pyrazoles, furan, and quinoline with strong coordination capability. The achievement of this methodology provides an efficient route to build new C(sp 3 )−heteroaryl bonds.

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Section: Introductionmentioning

confidence: 99%

Rh^III–Catalyzed Direct Heteroarylation of Unactivated C(sp³)–H with N-Heteroaryl Boronates

Chi,

Xu,

Liu

et al. 2024

J. Org. Chem.

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Rhodium‐Catalyzed C(sp ³ )H Functionalization

Chatani¹

2022

Handbook of CH-Functionalization

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Enormous progress has been made in the functionalization of CH bonds in the last two decades as testified by the great number of publications that have appeared in the literature. Herein, a comprehensive overview on the rhodium‐catalyzed functionalization of C(sp 3 )H bonds including activated C(sp 3 )H bonds, including a CH bond adjacent to a nitrogen atom or benzylic CH bond until spring 2021 is presented.

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Rhodium‐Catalyzed Cascade Radical Cyclization of 1,6‐Enynes with Br−CX₃: Access to Bromine‐Containing Trihalomethylated Pyrrolidines

et al. 2019

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We describe a novel rhodium(I)‐catalyzed cascade radical cyclization of 1,6‐enynes with Br−CX3 (X=Cl,Br). This transformation presents an efficient method for the construction of a variety of bromine‐containing trihalomethylated pyrrolidines in moderate to good yields. A possible radical pathway is proposed based on the relevant literature and control experiments. Moreover, this protocol is also applicable to 1,7‐enyne analogues.

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Rhodium(iii)-catalyzed unreactive C(sp³)–H alkenylation of N-alkyl-1H-pyrazoles with alkynes

Abstract: We report the first example of pyrazole-directed rhodium(iii)-catalyzed unreactive C(sp3)–H alkenylation with alkynes.

Cited by 14 publications

References 107 publications

Rh^III–Catalyzed Direct Heteroarylation of Unactivated C(sp³)–H with N-Heteroaryl Boronates

Rh^III–Catalyzed Direct Heteroarylation of Unactivated C(sp³)–H with N-Heteroaryl Boronates

Rhodium‐Catalyzed C(sp ³ )H Functionalization

Rhodium‐Catalyzed Cascade Radical Cyclization of 1,6‐Enynes with Br−CX₃: Access to Bromine‐Containing Trihalomethylated Pyrrolidines

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Rhodium(iii)-catalyzed unreactive C(sp3)–H alkenylation of N-alkyl-1H-pyrazoles with alkynes

Abstract: We report the first example of pyrazole-directed rhodium(iii)-catalyzed unreactive C(sp3)–H alkenylation with alkynes.

Cited by 14 publications

References 107 publications

RhIII–Catalyzed Direct Heteroarylation of Unactivated C(sp3)–H with N-Heteroaryl Boronates

RhIII–Catalyzed Direct Heteroarylation of Unactivated C(sp3)–H with N-Heteroaryl Boronates

Rhodium‐Catalyzed C(sp 3 )H Functionalization

Rhodium‐Catalyzed Cascade Radical Cyclization of 1,6‐Enynes with Br−CX3: Access to Bromine‐Containing Trihalomethylated Pyrrolidines

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Resources

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Rhodium(iii)-catalyzed unreactive C(sp³)–H alkenylation of N-alkyl-1H-pyrazoles with alkynes

Rh^III–Catalyzed Direct Heteroarylation of Unactivated C(sp³)–H with N-Heteroaryl Boronates

Rh^III–Catalyzed Direct Heteroarylation of Unactivated C(sp³)–H with N-Heteroaryl Boronates

Rhodium‐Catalyzed C(sp ³ )H Functionalization

Rhodium‐Catalyzed Cascade Radical Cyclization of 1,6‐Enynes with Br−CX₃: Access to Bromine‐Containing Trihalomethylated Pyrrolidines