Synthesis of oxygen heterocycles via Pd-catalyzed cross-coupling of unsaturated phenols and vinylic halides or triflates

Larock, Richard C.; Yang, Hoseok; Pace, Paola; Narayanan, K.; Russell, Charles E.; Cacchi, Sandro; Fabrizi, Giancarlo

doi:10.1016/s0040-4020(98)00399-8

Cited by 21 publications

(11 citation statements)

References 34 publications

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“…32,33) This reaction appears to proceed as depicted in Chart 6: oxidative addition of the hydroquinone 10 to Pd(0) and subsequent addition of the resulting arylpalladium complex to the carbon-carbon double bond of styrene derivative 11. 34) Subsequent intramolecular nucleophilic attack of the phenoxy group (2-hydroxyl group) on the σ-alkylpalladium intermediate (14) results in the observed dihydrobenzofuran and in regeneration of the Pd(0) catalyst. The high yield of dihydrobenzofuran can be probably accounted for by assuming that coordination of the phenolic (or phenoxy) group to the palladium in the σ-alkylpalladium intermediate (14) makes it difficult to achieve the conformation required for syn β-hydride elimination of one of the benzilic hydrogens.…”

Section: Resultsmentioning

confidence: 99%

Attempt to Synthesize 2,3,5,4′-Tetrahydroxystilbene Derived from 2,3,5,4′-Tetrahydroxystilbene-2-<i>O</i>-β-glucoside (THSG)

Tamura

Koshibe

Kaji

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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Section: Resultsmentioning

confidence: 99%

Attempt to Synthesize 2,3,5,4′-Tetrahydroxystilbene Derived from 2,3,5,4′-Tetrahydroxystilbene-2-<i>O</i>-β-glucoside (THSG)

Tamura

Koshibe

Kaji

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…As discussed earlier, the palladium-catalyzed couplings of alkenyl halides with alkenes can give rise to the formation of π-allylpalladium complexes, which can then be attacked by internal nucleophiles including hydroxy groups to yield various oxacyclic systems (Scheme 8.38) [343]. Lautens et al [344] reported the termination of a cascade of two intramolecular Heck 5-exo-trig carbopalladations by iodide leading from the o-bromobenzamide derivative 159 in the presence of potassium iodide to the heterotricycle 160 in 88% yield (Scheme 8.39).…”

Section: Palladium-catalyzed Reactions Involving Nucleophilic Substratesmentioning

confidence: 99%

Cross‐Coupling of Organyl Halides with Alkenes – The Heck Reaction

Bräse¹,

Meijere²

2013

Metal‐Catalyzed Cross‐Coupling Reactions and More

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The carbopalladation of an alkene by an organylpalladium halide is the essential step in one of the major contemporary metal-catalyzed C-C coupling reactions. About 45 years ago, a Japanese and an American group almost simultaneously designed and executed palladium-mediated coupling reactions of aryl and alkenyl halides with alkenes [1]. In subsequent investigations, Richard Heck and his group developed this reaction into a catalytic transformation and started to demonstrate its usefulness as well as its rather broad scope. The real push to utilize this powerful C-C-bondforming process, however, started only around the mid-1980s, and by now, an impressive number of publications have established the meanwhile so-called Heck reaction [2] 1) as an indispensable method in Organic Synthesis [3][4][5][6][7]. The universal recognition of the importance of the Heck reaction and the Negishi as well as the Suzuki coupling eventually won the Nobel Prize for Richard Heck along with Ei-ichi Negishi and Akira Suzuki in 2010. The applications of the Heck reaction range from the preparation of -functionalized and unfunctionalized -hydrocarbons, novel polymers, and dyes to new advanced enantioselective syntheses of natural products and biologically active nonnatural compounds. The more or less simultaneous developments of mechanistically related variants, namely, the Kumada, Suzuki, Stille, Hiyama, and Negishi coupling reactions (Chapters 12, 2, 3, 4, and 15, respectively) of metallated alkenes and arenes with aryl and alkenyl halides or the metal-catalyzed formation and cycloisomerization of enynes have drawn profit from the improvement of and mechanistic insights into the Heck reaction. This, of course, applies vice versa as well. Using only a catalytic amount of a palladium(0) complex or a precursor to a palladium species, the Heck reaction can bring about unprecedented structural changes, particularly when conducted intramolecularly. The full potential of this palladium-catalyzed process is still being further explored as demonstrated by a total of over 7000 publications in the past 40 years by 1) The alkynylation of aryl and alkenyl halides, frequently also considered as Heck reactions, is described in Chapter 6.

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“…67 In particular, the reaction conditions described above for the reaction of o-iodophenols with 1,3-dienes were successfully applied in the reaction between β-bromostyrene and o-vinylphenol to give the 2,3-dihydrobenzofuran 34 in an acceptable yield though a small amount (ca. 5%) of 2-benzyl-2H-1-benzopyran 35 was also observed (Scheme 33).…”

Section: Scheme 32mentioning

confidence: 99%