Olefin Hydroaryloxylation Catalyzed by Pincer–Iridium Complexes

Haibach, Michael C.; Guan, Changjian; Wang, David Y.; Li, Bo; Lease, Nicholas; Steffens, Andrew M.; Krogh‐Jespersen, Karsten; Goldman, Alan S.

doi:10.1021/ja404566v

Cited by 68 publications

(39 citation statements)

References 41 publications

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“…[1b] Hartwig has reported singular examples of Ir I -catalyzed hydroalkoxylations with moderate induction. [8] Alternative approaches to catalytic,stereo-or regioselective hydroalkoxylations rely on photocatalysis [9] or oxidation-reduction processes. [10,11] We now report the redox-neutral, asymmetric hydroalkoxylation of an on-activated alkene that is catalyzed by ac hiral titanium-carboxylate complex under thermally forcing conditions (220-240 8 8C).…”

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confidence: 99%

Asymmetric Hydroalkoxylation of Non‐Activated Alkenes: Titanium‐Catalyzed Cycloisomerization of Allylphenols at High Temperatures

et al. 2015

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The asymmetric catalytic addition of alcohols (phenols) to non-activated alkenes has been realized through the cycloisomerization of 2-allylphenols to 2-methyl-2,3-dihydrobenzofurans (2-methylcoumarans). The reaction was catalyzed by a chiral titanium-carboxylate complex at uncommonly high temperatures for asymmetric catalytic reactions. The catalyst was generated by mixing titanium isopropoxide, the chiral ligand (aS)-1-(2-methoxy-1-naphthyl)-2-naphthoic acid or its derivatives, and a co-catalytic amount of water in a ratio of 1:1:1 (5 mol % each). This homogeneous thermal catalysis (HOT-CAT) gave various (S)-2-methylcoumarans with yields of up to 90 % and in up to 85 % ee at 240 °C, and in 87 % ee at 220 °C.

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confidence: 99%

Asymmetric Hydroalkoxylation of Non‐Activated Alkenes: Titanium‐Catalyzed Cycloisomerization of Allylphenols at High Temperatures

et al. 2015

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“…of H 2 was observed. Presumably, a phenoxylation catalysed by silver is followed by a rapid dehydrogenative cyclization [20][21][22][23] . Detailed mechanistic aspects are currently under investigation (Fig.…”

Section: Resultsmentioning

confidence: 99%

A multitasking functional group leads to structural diversity using designer C–H activation reaction cascades

et al. 2014

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The C-H activation strategy has become one of the preferred methods to introduce chemical functionality to a chemically inert carbon atom. Intensive efforts have been devoted to developing either versatile bond formations (product structural diversity) or effective directing groups (substrate site selectivity). From the views of medicinal and synthetic practitioners, the C-H activation approach remains inadequate due to its limitation to pointto-point derivatization. Direct assembly of 3D molecular complexity in a single step remains elusive for this strategy. Towards this goal, a multitasking functional group is required to accomplish several missions in one pot: site selecitivity, cleavability and redox versatility. We demonstrate that an oxyacetamide group is such a multifunctional warhead that enables a series of C-H functionalization cascades and allows direct access to structurally diverse polycyclic heterocyles in one pot. The progress of these reaction cascades were fully controlled by oxidants and temperature. The proliferation of the reaction chain can be extended to a four-step cascade.

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“…Then, addition of a base and ClPR 2 yields the pincer ligand precursor which can be directly metalated (Scheme 2). This procedure has allowed the preparation of the corresponding Pd, [ 24,25 ] Pt, [ 25 ] and Ir [ 26–29 ] POCCH 2 P‐arylpincer compounds in good to excellent yields.…”

Section: Poczp‐aryl Pincer Metal Complexesmentioning

confidence: 99%

Hybrid POCZP Aryl Pincer Metal Complexes and their Catalytic Applications

et al. 2020

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The use of XCX‐aryl pincer metal complexes as catalysts started immediately after their discovery in 1976. Nowadays pincer metal complexes are commonly used as a new platform for the development and improvement of known and novel catalytic reactions. More recently, pincer metal complexes with hybrid pincer backbones of the type POCZP (Z = CH2, NH or S) have attracted much attention because of their facile preparation and outstanding catalytic performances. For instance, these complexes have been successfully used in cross‐coupling, transfer hydrogenation, and borylation reactions. In many cases, showing enhanced catalytic activities compared with POCOP‐ or PZCZP‐aryl pincer metal analogues. Hence, in this Minireview we summarize the available synthetic routes to produce POCZP aryl pincer ligands and their metal complexes as well as their applications as catalysts in different organic transformations.

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Olefin Hydroaryloxylation Catalyzed by Pincer–Iridium Complexes

Cited by 68 publications

References 41 publications

Asymmetric Hydroalkoxylation of Non‐Activated Alkenes: Titanium‐Catalyzed Cycloisomerization of Allylphenols at High Temperatures

Asymmetric Hydroalkoxylation of Non‐Activated Alkenes: Titanium‐Catalyzed Cycloisomerization of Allylphenols at High Temperatures

A multitasking functional group leads to structural diversity using designer C–H activation reaction cascades

Hybrid POCZP Aryl Pincer Metal Complexes and their Catalytic Applications

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