Ruthenium(II)‐Catalyzed C−H Bond [3+2] Annulation of <i>N</i>‐Nitrosoanilines with Alkynes in Water

Chen, Xun; Cui, Xuemin; Bai, Lili; Wang, Ying; Xie, Ying; Wang, Shuojin; Zhai, Ruirui; Zhao, Ke; Kong, Dulin; Li, Youbin

doi:10.1002/ajoc.201900553

Cited by 12 publications

(12 citation statements)

References 57 publications

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“…of NaOAc in 2 mL of H 2 O under air for 24 h (Scheme 46). [41] N ‐Nitrosoanilines bearing −Me and −OMe groups at para ‐position reacted very well with diphenyl acetylene ( 47 a ) to produce 48 a and 48 b in 78 and 81% yield, respectively. In the case of meta‐ Cl‐substituted N ‐nitrosoaniline, the C−H functionalization reaction occurred at the less sterically crowded position to form product 48 c .…”

Section: Miscellaneous Catalysismentioning

confidence: 99%

Recent Advances and Strategies for the Transition‐Metal‐Catalyzed C−H Functionalization of N‐Nitrosoanilines

et al. 2021

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The challenges faced in the activation and functionalization of C−H bonds while producing high‐value aromatic intermediates are significant for synthetic organic chemistry. This review summarizes the advancements made toward the C−H functionalization of N‐nitrosoanilines in the past decade, in which the nitroso group coordinates to a transition metal, such as rhodium, palladium, cobalt, iridium, and ruthenium, acting as a directing group to allow the activation of the ortho C−H bond. The versatility of this synthetic approach has led to the regio‐ and chemoselective introduction of various functional groups giving rise to aromatic congeners with diverse functional and structural properties. C−H functionalized nitroso compounds can be further transformed into valuable synthetic intermediates and unique heterocyclic compounds. A description of the mechanism underlying each reaction is also included. This review includes the following sections:

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Section: Miscellaneous Catalysismentioning

confidence: 99%

Recent Advances and Strategies for the Transition‐Metal‐Catalyzed C−H Functionalization of N‐Nitrosoanilines

et al. 2021

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“…Cu(OAc) 2 and 0.2 eq. NaOAc in water for 24 h (Scheme 21, Condition B) [53] . Several electron‐donating substituents (Me, OMe etc.)…”

Section: N‐nitroso As a Traceless Directing Groupmentioning

confidence: 99%

“…NaOAc in water for 24 h (Scheme 21, Condition B). [53] Several electron-donating substituents (Me, OMe etc.) on the aryl ring afforded better cycloadducts than electron-withdrawing groups.…”

Section: Ortho-cyclizationmentioning

confidence: 99%

N‐Nitroso As A Novel Directing Group in Transition‐Metal‐Catalyzed C(sp²)−H Bond Functionalizations of N‐Nitrosoanilines

2021

Asian J Org Chem

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In the last few decades, the syntheses of bioactive natural products and functional materials have been achieved via CÀ H bond functionalizations where the transition metals in coordination with the directing groups trigger the CÀ H bond activation. A wide variety of directing groups has been recognized for transition-metal-catalyzed ortho-CÀ H bond functionalization of arenes. Recently, N-nitroso group has been established as a new, efficient and sometimes as a traceless directing group in ortho-C(sp 2 )À H bond functionali-zations of N-nitrosoanilines. During functioning as a tracelessdirecting-group, the N -O bond of N-nitrosoaniline acts as an internal oxidant to recycle the employed catalyst. Pd, Rh, Co, Ru and Ir catalysts have been screened for the ortho CÀ H bond functionalizations of N-nitrosoanilines constructing new CÀ C, CÀ O, CÀ N and CÀ X bonds. Herein, we have summarized all the recently developed N-nitroso group directed ortho-C(sp 2 )À H bond functionalization reactions of N-nitrosoanilines.

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“…Co 41 [24] R = boc Rh 7 and 8 [13,25] In situ hydrazone Rh 11a [26] Ru 37 [27] Co 43 [28] Rh 10 [14] Rh 12a and 12b [29] Intramolecular annulation Rh 13, 15a, and 15b [30,31] Rh 16,18,19,21,22,23,24, and 27 [32][33][34][35][36][37][38][39] Rh 25 [40] In situ N-nitrosoaniline Rh 26 [41] Intramolecular annulation Ru 40 [42] Co 45 and 46 [43,44] Rh 33 [45] the cleavage of N-N bond are found in the literature. [53] But no report portrayed a N-N σ-bond as an internal oxidising DG until Glorius and co-workers reported a rhodium (III)-catalysed annulation of hydrazides with internal alkynes to afford 2,3-disubstituted indoles.…”

Section: R = Acmentioning

confidence: 99%

Recent advances in the synthesis of indoles via C–H activation aided by N–N and N–S cleavage in the directing group

Sarmah

Tahu

Bora

2021

Applied Organom Chemis

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Transition metal‐catalysed C–H activation strategies with the use of diverse directing groups have emerged as regioselective, chemoselective, and step economic tools for the synthesis of the biologically relevant indole nucleus. This review highlights the synthesis of indoles using C–H activation assisted by directing groups containing N–N and N–S bonds. An N‐atom within the directing group transforms into the indolyl nitrogen while the cleaving N–N/N–S bonds within the directing group act as internal oxidants for the completion of the catalytic turnover.

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Ruthenium(II)‐Catalyzed C−H Bond [3+2] Annulation of N‐Nitrosoanilines with Alkynes in Water

Cited by 12 publications

References 57 publications

Recent Advances and Strategies for the Transition‐Metal‐Catalyzed C−H Functionalization of N‐Nitrosoanilines

Recent Advances and Strategies for the Transition‐Metal‐Catalyzed C−H Functionalization of N‐Nitrosoanilines

N‐Nitroso As A Novel Directing Group in Transition‐Metal‐Catalyzed C(sp²)−H Bond Functionalizations of N‐Nitrosoanilines

Recent advances in the synthesis of indoles via C–H activation aided by N–N and N–S cleavage in the directing group

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Ruthenium(II)‐Catalyzed C−H Bond [3+2] Annulation of N‐Nitrosoanilines with Alkynes in Water

Cited by 12 publications

References 57 publications

Recent Advances and Strategies for the Transition‐Metal‐Catalyzed C−H Functionalization of N‐Nitrosoanilines

Recent Advances and Strategies for the Transition‐Metal‐Catalyzed C−H Functionalization of N‐Nitrosoanilines

N‐Nitroso As A Novel Directing Group in Transition‐Metal‐Catalyzed C(sp2)−H Bond Functionalizations of N‐Nitrosoanilines

Recent advances in the synthesis of indoles via C–H activation aided by N–N and N–S cleavage in the directing group

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N‐Nitroso As A Novel Directing Group in Transition‐Metal‐Catalyzed C(sp²)−H Bond Functionalizations of N‐Nitrosoanilines