A synthesis of biaryls via nickel(0)-catalyzed cross-coupling reaction of chloroarenes with phenylboronic acids

Saito, Shota; Sakai, Masaaki; Miyaura, Norio

doi:10.1016/0040-4039(96)00482-0

Cited by 144 publications

(47 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…As seen in Table 2, steric effects were observed as the ortho-substituted aryl chlorides gave lower yields than their para-substituted analogs (entries 1 and 2, 3 and 4, 6 and 7, respectively). [9,32] The coupling of 4-chlorobiphenyl, 1,4-dichlorobenzene, 1,3,5-trichlorobenzene and 1,2,4,5-tetrachlorobenzene with phenylboronic acid gave the corresponding polyphenyls in good to excellent yields (72-91%, entries [15][16][17][18], which suggests that this catalytic protocol was efficient in the formation of polyaryls. These results confirm that in contrast to Pd-catalyzed cross-coupling of aryl chlorides with arylboronic acids where aryl chlorides with electron-donating groups are generally not reactive, [15,31] Ni Ni PPh 3 Ph 3 P Cl 1 Figure 1.…”

Section: Resultsmentioning

confidence: 92%

Suzuki–Miyaura coupling reactions of aryl chlorides catalyzed by a new nickel(II) σ‐aryl complex

Lei

Obregon

Alla

2013

Applied Organom Chemis

View full text Add to dashboard Cite

A new nickel(II) s-aryl complex, trans-chloro(9-phenanthrenyl)bis(triphenylphosphine)nickel(II), was used as a precatalyst for the Suzuki-Miyaura coupling reactions of aryl chlorides. The catalytic conditions were optimized by investigating the crosscoupling of p-chloroanisole with phenylboronic acid. The results show that this complex is efficient for both electron-rich and electron-deficient aryl chlorides, though it gives better yields for activated arylboronic acids than deactivated ones. All isolated cross-coupled biaryl products have been characterized by 1 H and 13 C NMR, and their spectral data are consistent with those reported. Side products from the coupling of arylboronic acid with the precatalyst complex have also been isolated and characterized, which is helpful for understanding the coupling mechanism.

show abstract

Section: Resultsmentioning

confidence: 92%

Suzuki–Miyaura coupling reactions of aryl chlorides catalyzed by a new nickel(II) σ‐aryl complex

Lei

Obregon

Alla

2013

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…Recently, cross-coupling with organoboranes has been optimized as being applicable for aryl chlorides (entries 1-5) [47][48][49][50][51][52] and aryl sulfonates (entries 6-10) [53][54][55][56][57], without any loss of efficiency. Compared with an aryl Grignard reagent, the reactivity of arylborane towards aryl chloride is different.…”

Section: Cross-coupling Of Aryl Electrophiles With Organometallic Commentioning

confidence: 99%

Nickel‐Catalyzed Cross‐Coupling Reactions

Takahashi¹,

Kanno²

2005

Modern Organonickel Chemistry

View full text Add to dashboard Cite

“…Activated aryl chlorides react much like unactivated aryl bromides, and reactions of these substrates with the original catalyst based on tri-ortho-tolyl phosphine were reported [143]. Nickel complexes are also known to react readily with aryl chlorides in cross-coupling chemistry [144][145][146][147][148][149], and they have also been used in the catalyzed amination of aryl chlorides [82,83]. In general, the nickel-catalyzed chemistry occurs with lower turnover numbers and has a narrower substrate scope than the palladium-catalyzed reactions with third-generation ligands.…”

Section: Use Of Sterically Hindered Bis(phosphine) Ligandsmentioning

confidence: 99%

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Hartwig

2002

Modern Arene Chemistry

View full text Add to dashboard Cite

The transition metal catalyzed synthesis of arylamines by the reaction of aryl halides or triflates with primary or secondary amines has become a valuable synthetic tool for many applications. This process forms monoalkyl or dialkyl anilines, mixed diarylamines or mixed triarylamines, as well as N-arylimines, carbamates, hydrazones, amides, and tosylamides. The mechanism of the process involves several new organometallic reactions. For example, the CaN bond is formed by reductive elimination of amine, and the metal amido complexes that undergo reductive elimination are formed in the catalytic cycle in some cases by NaH activation. Side products are formed by b-hydrogen elimination from amides, examples of which have recently been observed directly. An overview that covers the development of synthetic methods to form arylamines by this palladium-catalyzed chemistry is presented. In addition to the synthetic information, a description of the pertinent mechanistic data on the overall catalytic cycle, on each elementary reaction that comprises the catalytic cycle, and on competing side reactions is presented. The review covers manuscripts that appeared in press before June 1, 2001. This chapter is based on a review covering the literature up to September 1, 1999. However, roughly one-hundred papers on this topic have appeared since that time, requiring an updated review.

show abstract

A synthesis of biaryls via nickel(0)-catalyzed cross-coupling reaction of chloroarenes with phenylboronic acids

Cited by 144 publications

References 10 publications

Suzuki–Miyaura coupling reactions of aryl chlorides catalyzed by a new nickel(II) σ‐aryl complex

Suzuki–Miyaura coupling reactions of aryl chlorides catalyzed by a new nickel(II) σ‐aryl complex

Nickel‐Catalyzed Cross‐Coupling Reactions

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Contact Info

Product

Resources

About