Palladium-Catalyzed Cross-Coupling Reactions of Organoboronic Acids with Organic Electrophiles.

Martin, Arnold R.; Yang, Y.; Spinelli, Domenico; Frenna, Vincenzo; Consiglio, Giovanni; Chanon, Michel; Striley, Cindy; Weidlein, Johann; Nasiri, Ahmad; Okada, Yoshito

doi:10.3891/acta.chem.scand.47-0221

Cited by 206 publications

(87 citation statements)

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“…Another heterocyclic carbene complex of type 15 has been used for the SM coupling of aryl chlorides, with turnover frequencies up to 552. 29 Trudell and co-workers 30 have found that the SM crosscoupling reaction of the arylboronic acids with nonactivated aryl chlorides occurs at 808C in high yields if catalytic amounts of Pd 2 (dba) 3 and the sterically crowded imidazolium salt 16 are combined with Cs 2 CO 3 in dioxane. Both sterically hindered and electron-rich aryl chlorides were found to couple with arylboronic acids in high yields.…”

Section: Sm Coupling Reactions With Aryl Chloridesmentioning

confidence: 99%

“…This protocol is applicable to electron-poor and electron-rich substrates with equal ease. Littke and Fu reported that P(t-Bu) 3 is an efficient ligand for the Pd-catalysed reactions of various aryl chlorides with arylboronic acids in dioxane/Pd 2 (dba) 3 /Cs 2 CO 3 (Scheme 15). P(t-Bu) 3 is however pyrophoric and needs special precautions while handling.…”

Section: Sm Coupling Reactions With Aryl Chloridesmentioning

confidence: 99%

“…Littke and Fu reported that P(t-Bu) 3 is an efficient ligand for the Pd-catalysed reactions of various aryl chlorides with arylboronic acids in dioxane/Pd 2 (dba) 3 /Cs 2 CO 3 (Scheme 15). P(t-Bu) 3 is however pyrophoric and needs special precautions while handling. 34 The high activity of P(t-Bu) 3 was attributed to the electron-rich nature and the steric bulk of the ligand.…”

Section: Sm Coupling Reactions With Aryl Chloridesmentioning

confidence: 99%

“…23 have recently applied the concept of directed ortho-metallation of arenes in which the neopentyl ester acts as an efficient ortho directing group for the ortho metallation of arenes using lithium diisopropylamide (LDA) as a base and triisopropylborate B(OiPr) 3 , as an in situ trap. The crude boronic acid was complexed with diethanolamine to deliver 9 (Scheme 9).…”

Section: Caron and Hawkinsmentioning

confidence: 99%

“…In such instances, Ba(OH) 2 or K 3 PO 4 has been used to generate good yields of the cross-coupling products. Other bases utilised in the SM coupling reaction include Cs 2 CO 3 , K 2 CO 3 , TlOH, KF and NaOH.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,635

530

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Section: Sm Coupling Reactions With Aryl Chloridesmentioning

confidence: 99%

Section: Sm Coupling Reactions With Aryl Chloridesmentioning

confidence: 99%

Section: Sm Coupling Reactions With Aryl Chloridesmentioning

confidence: 99%

Section: Caron and Hawkinsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,635

530

View full text Add to dashboard Cite

Trace impurities identified by high performance liquid chromatography/electrospray mass spectrometry in two different synthetic batches of 4-boronophenylalanine

Vähätalo

Tuominen

Kokkonen

et al. 1998

Rapid Commun. Mass Spectrom.

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The chemical purity of two synthetic 4-boronophenylalanine (BPA, C 9 H 12 O 4 BN) batches produced by two different pathways were investigated by high performance liquid chromatography/electrospray mass spectrometry. Currently, BPA is one of the most important clinical boron carriers in boron neutron capture therapy (BNCT). Low energy tandem mass spectrometry was used to elucidate the structure of BPA and two minor signals eluting later than the major compound. In the mass spectrom a very intense singly charged [MH] ion m/z 209 was observed. The ratio of 10 B/ 11 B was estimated also. The product-ion spectrum of BPA shows distinct losses of 18, 46 and 89 u. Based on the fragmentation of the major compound two impurities were characterized. In both cases an intense molecular ion, 244 u and 285 u was observed. Knowing the synthetic pathway and fragmentation of the major compound we suggest the following formulae for the impurities: C 9 H 10 O 2 BrN and C 15 H 16 O 4 BN. Further evidence to the first impurity is the detected isotope pattern, corresponding to bromine. The existence of the impurities can be explained and avoided by exploring the synthetic pathways used. High performance liquid chromatography/electrospray mass spectrometry was demonstrated to be an important novel analytical instrument to check the purity of BPA prior to clinical studies in BNCT. #

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Cesium Carbonate

Sivik

Ghosh

Sarkar

Encyclopedia of Reagents for Organic Synthesis

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Palladium-Catalyzed Cross-Coupling Reactions of Organoboronic Acids with Organic Electrophiles.

Cited by 206 publications

References 0 publications

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Trace impurities identified by high performance liquid chromatography/electrospray mass spectrometry in two different synthetic batches of 4-boronophenylalanine

Cesium Carbonate

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