A new approach to the solid-phase Suzuki coupling reaction

Piettre, Serge R.; Baltzer, S.

doi:10.1016/s0040-4039(97)00063-4

Cited by 84 publications

(35 citation statements)

References 21 publications

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“…Coupling of iodide 28 with compound 30 proceeded well in the presence of [Pd(PPh 3 ) 4 ] in DMF/water (6:1) and with K 2 CO 3 as base. [18] Application of Methods A, B, and D yielded biphenyl 44 in overall yields of 60 ± 93 %. Thienylboronic acid (31) was used to investigate the compatibility of the oxidative cleavage conditions with oxidation-sensitive compounds.…”

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confidence: 99%

Development of the Traceless Phenylhydrazide Linker for Solid‐Phase Synthesis

Stieber¹,

Grether²,

Waldmann³

2003

Chemistry A European J

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The hydrazide group is a new oxidatively cleavable traceless linker for solid-phase chemistry. It can be readily introduced by hydrazide formation between a carboxy-functionalized resin and different substituted hydrazines. In order to achieve high yields in this step, new carboxylic acid resins were developed that are not prone to undesired imide formation upon activation of the carboxylic acid. The polymer-bound acyl hydrazides were successfully employed in various transformations, namely Heck, Suzuki, Sonogashira, and Stille couplings, as well as Wittig and Grignard reactions. Traceless release of the coupling products from the solid support is achieved selectively under mild conditions and in high purity by oxidation of the aryl hydrazides to acyl diazenes with Cu(II) salts or N-bromosuccinimide (NBS) and subsequent nucleophilic attack of the acyl diazene intermediates. Traceless cleavage by oxidation with NBS can be carried out as a two-step process in which stable acyl diazenes are first generated by treatment with NBS in the absence of a nucleophile. After removal of the reagents by simple resin washing, the traceless release is effected by the addition of methanol, which leads to products of high purity without any additional separation steps.

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Development of the Traceless Phenylhydrazide Linker for Solid‐Phase Synthesis

Stieber¹,

Grether²,

Waldmann³

2003

Chemistry A European J

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“…In these cases the ligand molecules associate themselves spontaneously with the air-stable Pd salt if co-solvated in an appropriate solvent. Various bases have been used as co-catalysts, among them KOH [43], Na 2 CO 3 [7,15], K 2 CO 3 [8,9,44], KHCO 3 [44], Ba(OH) 2 [29], NEt 3 , CsF [45,46], KF [8], and K 3 PO 4 [6,8,20,21,24]. Unfortunately their impact on the yield of a given coupling and the purity of the final products are difficult to estimate [47].…”

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confidence: 99%

“…A more attractive method, perhaps, may be conversion of an aryl halide with commercially available bis(pinacolato)diboron [50,51]. This method was even used to generate boronates from iodides [6,51] bound to polymeric supports, where the classical method was unsuccessful [6]. Of general concern during Suzuki couplings is the air sensitivity of the reaction mixture and the reagents.…”

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CC Bond‐Forming Reactions

Brill¹,

Papeo²

2006

Combinatorial Chemistry

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“…To this end, first the carboxyl group of the linker was esterified with m-iodobenzylbromide 8 and the polymer-bound aryl iodide 9 generated was then further transformed by Heck [10] , Suzuki [11] or Sonogashira [12] reactions (Scheme 3). NMR spectroscopic analysis revealed that these transformations proceeded quantitatively.…”

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confidence: 99%

“…In a third series of experiments we investigated whether the enzymatic method also gives access to target molecules that are coupled to the linker as amides. To this end, 4-iodoaniline 22 was coupled quantitatively to linker 7 and the polymerfixed aryliodide 23 obtained thereby was subjected to a Suzuki reaction [11] with 4-methoxyphenyl boronic acid or a Shille reaction [13] to give enol ether 26 (Scheme 5). Upon treatment with 0.5 m hydrochloric acid, enol ether 26 yielded acetophenone 27, thereby proving the acid stability of the linker.…”

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confidence: 99%