One‐Pot Dual Substitutions of Bromobenzyl Chloride, 2‐Chloromethyl‐6‐halogenoimidazo[1,2‐<i>a</i>]pyridine and ‐[1,2‐<i>b</i>]pyridazine by Suzuki–Miyaura Cross‐Coupling Reactions

A simple and efficient iron‐catalyzed method for arylation of aromatic carbonyl compounds is reported. The use of 4 % FeCl3 or Fe(acac)3 as the catalyst, in combination with a slight excess of chlorotrimethylsilane and triethylsilane, chlorination of benzylic ketones and aldehydes with subsequent Friedel–Crafts alkylation of arenes is achieved. Although the method is limited by the general constraints associated with Friedel–Crafts alkylation reactions, robust applications for the synthesis of pharmaceutical intermediates and so on can be envisioned.

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“…R f = 0.70 (dichloromethane/hexane, 1:3). Characterization data is consistent with that published previously 37…”

Section: Methodssupporting

confidence: 92%

Iron‐Catalyzed Arylation of Aromatic Ketones and Aldehydes Mediated by Organosilanes

2014

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“…were oxidized, giving the already known benzophenone (18) and the expected 3-benzoylbenzoic acid (19) due to the additional oxidation of the methyl group. Because of this and taking into account that oxygen-bearing substituents like methoxy or nitro were not compatible with the latest reaction conditions [23], oxidation with chromium (VI) oxide (CrO 3 ) in acetic acid [24] was used in these special cases (9, 13 and 14).…”

Section: Methodsmentioning

confidence: 99%

Ultrasound promoted Barbier reactions and Csp3–Csp2 Stille coupling for the synthesis of diarylmethanes and substituted benzophenones

Ocampo

Koll

Mandolesi

2013

Ultrasonics Sonochemistry

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Here we present the preparation of a variety of diarylmethanes obtained via ultrasound Stille coupling under palladium catalysis between some substituted aryl compounds and benzyltributyltin compounds generated through sonicated Barbier reaction in a very short time reaction and excellent yield. The study reported below compares different methods to optimize the synthesis of usually unstable benzyltin derivatives and is another contribution to the investigation of Csp(3)-Csp(2) coupling process involving benzyl-aryl reagents. Substituted carboxylated benzophenones were easily prepared in a very good yield by oxidation of some diarylmethanes.

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“…Gueiffier and co‐workers described one‐pot dual substitution of 6‐bromo‐2‐(chloromethyl)imidazo[1,2‐ a ]pyridine ( 167 ) by Suzuki–Miyaura cross‐coupling reactions 97. Thus, 167 was treated with one equivalent of an arylboronic acid [Ar 1 B(OH) 2 ] in the presence of Pd(PPh 3 ) 4 (2 mol‐%) and 2.1 equiv.…”

Section: Regiocontrolled Double Functionalization By Means Of Metamentioning

confidence: 99%

Functionalization of Imidazo[1,2‐a]pyridines by Means of Metal‐Catalyzed Cross‐Coupling Reactions

et al. 2014

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One‐Pot Dual Substitutions of Bromobenzyl Chloride, 2‐Chloromethyl‐6‐halogenoimidazo[1,2‐a]pyridine and ‐[1,2‐b]pyridazine by Suzuki–Miyaura Cross‐Coupling Reactions

Abstract: A very simple, mild and inexpensive palladium-catalyzed cross-coupling of (hetero)arylboronic acids with benzylic halides occurs in good yield. This method was successfully expanded to two heterocyclic electrophiles and allowed onepot dual substitutions of bromobenzyl chloride, 2-chlo-

Cited by 46 publications

References 19 publications

Iron‐Catalyzed Arylation of Aromatic Ketones and Aldehydes Mediated by Organosilanes

Iron‐Catalyzed Arylation of Aromatic Ketones and Aldehydes Mediated by Organosilanes

Ultrasound promoted Barbier reactions and Csp3–Csp2 Stille coupling for the synthesis of diarylmethanes and substituted benzophenones

Functionalization of Imidazo[1,2‐a]pyridines by Means of Metal‐Catalyzed Cross‐Coupling Reactions

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