2013
DOI: 10.1002/chem.201301988
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Ruthenium(II)‐Catalyzed CH Alkenylations of Phenols with Removable Directing Groups

Abstract: Cationic ruthenium(II) complexes enabled oxidative alkenylations of phenols bearing easily cleavable directing groups. The optimized catalytic system allowed twofold CH bond activations with excellent chemo-, site-, and diastereoselectivities. The double CH functionalization process proceeded efficiently in an aerobic fashion under an atmosphere of ambient air. Detailed mechanistic studies were performed and provided strong support for an initial reversible CH bond activation by the formation of six-membere… Show more

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Cited by 101 publications
(27 citation statements)
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“…[11] Using a 2-pyridyl protecting group (Pyr), the selective ortho olefination of a variety of aromatic and heteroaromatic compounds could be achieved. [11] Using a 2-pyridyl protecting group (Pyr), the selective ortho olefination of a variety of aromatic and heteroaromatic compounds could be achieved.…”
mentioning
confidence: 99%
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“…[11] Using a 2-pyridyl protecting group (Pyr), the selective ortho olefination of a variety of aromatic and heteroaromatic compounds could be achieved. [11] Using a 2-pyridyl protecting group (Pyr), the selective ortho olefination of a variety of aromatic and heteroaromatic compounds could be achieved.…”
mentioning
confidence: 99%
“…Quite recently, the group of Ackermann extended the substrate scope to protected phenols. [11] Using a 2-pyridyl protecting group (Pyr), the selective ortho olefination of a variety of aromatic and heteroaromatic compounds could be achieved. This procedure made use of over-stoichiometric amounts of Cu II salts.…”
mentioning
confidence: 99%
“…Thev ersatile ruthenium(II) oxidase catalysis was not limited to the preparation of benzannulated heterocycles 3. Indeed, the aerobic C À Hf unctionalization also enabled aerobic alkenylations of phenol derivatives 4 [16] having ar emovable directing group (Scheme 2; Table S2). Thus, single-component ruthenium(II) biscarboxylates [17] could be used to successfully catalyze reactions with excellent chemoand positional selectivity.…”
Section: Methodsmentioning
confidence: 98%
“…[21,22] For instance, we have devised reaction conditions for step-economi-cal direct arylations [21] as well as alkenylations. [22] In consideration of the practical importance of substituted phenols and catechols, we became interested in exploring the use of the 2pyridyloxy substituent as a removable auxiliary for oxidative CÀH functionalization reactions that lead to CÀO-bond formation. As part of our ongoing research program on step-economical CÀH functionalizations, [23,24] we report herein the development of a protocol for the efficient oxygenation of unactivated aromatic CÀH bonds in 2-pyridyloxyarenes.…”
Section: Introductionmentioning
confidence: 99%