Palladium-catalyzed acylative cross-coupling of amides with diarylborinic acids and sodium tetraarylborates

Li, Xijing; Zou, Gang

doi:10.1016/j.jorganchem.2015.07.009

Cited by 65 publications

(21 citation statements)

References 70 publications

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“…The acyl Suzuki cross-coupling of higher order aryl boron reagents with amides was reported by Zou (Scheme 25) [93]. With the use of N-3,5(CF 3 ) 2 C 6 H 3 activating group and Pd(PCy 3 ) 2 Cl 2 /PCy 3 catalyst system they were able to overcome the electronic and steric factors for the cross-coupling of amides with diarylborinic acids or tetra-arylborates to synthesize ketones (Scheme 25A).…”

Section: Suzuki Cross-coupling Of Amidesmentioning

confidence: 99%

Recent Advances in Acyl Suzuki Cross-Coupling

2019

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Acyl Suzuki cross-coupling involves the coupling of an organoboron reagent with an acyl electrophile (acyl halide, anhydride, ester, amide). This review provides a timely overview of the very important advances that have recently taken place in the acylative Suzuki cross-coupling. Particular emphasis is directed toward the type of acyl electrophiles, catalyst systems and new cross-coupling partners. This review will be of value to synthetic chemists involved in this rapidly developing field of Suzuki cross-coupling as well as those interested in using acylative Suzuki cross-coupling for the synthesis of ketones as a catalytic alternative to stoichiometric nucleophilic additions or Friedel-Crafts reactions.

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Section: Suzuki Cross-coupling Of Amidesmentioning

confidence: 99%

Recent Advances in Acyl Suzuki Cross-Coupling

2019

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“…[57] In 2015, the Zou group reported the first Pd-catalyzed Suzuki cross-coupling of N-Ts/Ph amides (Scheme 20). [72] In the same year,t he Garg group developedt he first Ni-catalyzed Suzuki-cross-coupling of N-Boc/alkyl amides (Scheme 21). The cross-coupling of sterically hindered amide substrates was accomplished by using electron-withdrawing aromatic substituents at the amide nitrogen.…”

Section: Cross-coupling Of N-glutarimide Amidesmentioning

confidence: 99%

“…The cross‐coupling of sterically hindered amide substrates was accomplished by using electron‐withdrawing aromatic substituents at the amide nitrogen. This suggests that oxidative addition into the N−C bond is slow under these conditions …”

Section: Twisted Amides In Catalytic N−c Amide Bond Cross‐couplingmentioning

confidence: 99%

Twisted Amides: From Obscurity to Broadly Useful Transition‐Metal‐Catalyzed Reactions by N−C Amide Bond Activation

Liu

Szostak

2017

Chemistry A European J

297

176

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The concept of using amide bond distortion to modulate amidic resonance has been known for more than 75 years. Two classic twisted amides (bridged lactams) ingeniously designed and synthesized by Kirby and Stoltz to feature fully perpendicular amide bonds, and as a consequence emanate amino-ketone-like reactivity, are now routinely recognized in all organic chemistry textbooks. However, only recently the use of amide bond twist (distortion) has advanced to the general organic chemistry mainstream enabling a host of highly attractive N-C amide bond cross-coupling reactions of broad synthetic relevance. In this Minireview, we discuss recent progress in this area and present a detailed overview of the prominent role of amide bond destabilization as a driving force in the development of transition-metal-catalyzed cross-coupling reactions by N-C bond activation.

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“…Early this year, Rueping and co-workers described the other nickel-catalyzed cross-coupling of B-alkyl-9-BBN with amides [ 27 ]. After extension of the nucleophile counterparts from arylboronic acids to cost-effective diarylborinic acids and tetraarylboronates in palladium-catalyzed acylative cross-coupling of amides [ 28 , 29 ], we are interested in the reactivity of trialkylboranes, which could be readily prepared from alkyl Grignard reagents or olefins via hydroboration. Herein we report a highly efficient palladium-catalyzed acylative cross-coupling of activated amides with trialkylboranes at room temperature by using 1,3-bis(2,6-diisopropyl)phenylimidazolylidene (IPr) and 3-chloropyridine (3-ClPy) co-supported palladium chloride, the PEPPSI catalyst developed by Organ et al [ 30 ].…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes

Shi

Zou

2018

Molecules

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A highly efficient acylative cross-coupling of trialkylboranes with activated amides has been effected at room temperature to give the corresponding alkyl ketones in good to excellent yields by using 1,3-bis(2,6-diisopropyl)phenylimidazolylidene and 3-chloropyridine co-supported palladium chloride, the PEPPSI catalyst, in the presence of K2CO3 in methyl tert-butyl ether. The scope and limitations of the protocol were investigated, showing good tolerance of acyl, cyano, and ester functional groups in the amide counterpart while halo group competed via the classical Suzuki coupling. The trialkylboranes generated in situ by hydroboration of olefins with BH3 or 9-BBN performed similarly to those separately prepared, making this protocol more practical.

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Palladium-catalyzed acylative cross-coupling of amides with diarylborinic acids and sodium tetraarylborates

Cited by 65 publications

References 70 publications

Recent Advances in Acyl Suzuki Cross-Coupling

Recent Advances in Acyl Suzuki Cross-Coupling

Twisted Amides: From Obscurity to Broadly Useful Transition‐Metal‐Catalyzed Reactions by N−C Amide Bond Activation

Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes

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