2018
DOI: 10.3390/molecules23020433
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Pd-Catalyzed, Highly Selective C(sp2)-Br Bond Coupling Reactions of o-(or m-, or p-) Chloromethyl Bromobenzene with Arylboronic Acids

Abstract: Highly selective C(sp2)–C(sp2) cross-coupling of dihalogenated hydrocarbons comprising C(sp2)–Br and C(sp3)–Cl bonds with arylboronic acids is reported. This highly selective coupling reaction of the C(sp2)–Br bond is successfully achieved using Pd(OAc)2 and PCy3·HBF4 as the palladium source and ligand, respectively. A series of chloromethyl-1,1′-biphenyl compounds are obtained in moderate-to-excellent yields. Moreover, this protocol can be extended to the one-pot dual arylation of 1-bromo-4-(chloromethyl)benz… Show more

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Cited by 5 publications
(3 citation statements)
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References 44 publications
(38 reference statements)
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“…Note: trimethylphosphine is a pyrophoric compound and should be handled carefully by appropriately trained individuals using inert atmosphere techniques. To prepare comonomer f , 4-chloromethyl-4′-vinyl-1,1′-biphenyl ( f′ ) was first synthesized based on a Suzuki-Miyaura coupling procedure reported by Pei and co-workers . The Suzuki-Miyaura product f′ underwent a nucleophilic substitution reaction with trimethylphosphine in anhydrous toluene as described above, yielding comonomer f .…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…Note: trimethylphosphine is a pyrophoric compound and should be handled carefully by appropriately trained individuals using inert atmosphere techniques. To prepare comonomer f , 4-chloromethyl-4′-vinyl-1,1′-biphenyl ( f′ ) was first synthesized based on a Suzuki-Miyaura coupling procedure reported by Pei and co-workers . The Suzuki-Miyaura product f′ underwent a nucleophilic substitution reaction with trimethylphosphine in anhydrous toluene as described above, yielding comonomer f .…”
Section: Methodsmentioning
confidence: 99%
“…A general nucleophilic substitution was performed as To prepare comonomer f, 4-chloromethyl-4′-vinyl-1,1′-biphenyl (f′) was first synthesized based on a Suzuki-Miyaura coupling procedure reported by Pei and co-workers. 38 The Suzuki-Miyaura product f′ underwent a nucleophilic substitution reaction with trimethylphosphine in anhydrous toluene as described above, yielding comonomer f. Detailed synthetic procedures and spectroscopic characterization of f′ and f are provided in Section A of the Supporting Information. Synthesis of StyDex Polymers.…”
Section: ■ Introductionmentioning
confidence: 99%
“…In the second step, bromine at para position is used for the Suzuki C–C coupling reaction, as shown in Scheme . It is also used as an intermediate in other N -alkylations, S -alkylations, and most importantly in C–C cross-coupling reactions. …”
Section: Introductionmentioning
confidence: 99%