Pd(0)–Cu(I)-catalyzed cross-coupling of alkynylsilanes with triarylantimony(V) diacetates

Kang, Suk‐Ku; Ryu, Hyung-Chul; Hong, Young‐Taek

doi:10.1039/b007800j

Cited by 54 publications

(26 citation statements)

References 17 publications

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“…They replaced the commonly used aryl halides in the coupling with organoantimony compounds, namely triarylantimony diacetates (45) [28]. The reaction of 45 with alkynylsilanes (44) palladium(0) complex and copper iodide gave a disubstituted acetylene derivative (46).…”

Section: Sequential Coupling Reactionsmentioning

confidence: 99%

Sequential and domino Sonogashira coupling: Efficient tools for the synthesis of diarylalkynes

Nagy

Novàk

Kotschy

2005

Journal of Organometallic Chemistry

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Section: Sequential Coupling Reactionsmentioning

confidence: 99%

Sequential and domino Sonogashira coupling: Efficient tools for the synthesis of diarylalkynes

Nagy

Novàk

Kotschy

2005

Journal of Organometallic Chemistry

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“…However, to the best of our knowledge, only a few examples of Pd-catalyzed carbonylative coupling reaction by use of organoantimony compounds have been reported to date. For instance, triarylantimony diacetates were successfully coupled under CO atmosphere with alkynylsilanes [8] to form alkynyl ketones and organostannanes [9] to give aryl-and vinyl ketones. We have also recently demonstrated a new carbonylative cross-coupling reaction between ethynylstibanes and aryl iodides to give ethynyl ketones [10].…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed carbonylative cross-coupling reaction of triarylantimony dicarboxylates with arylboronic acids: Synthesis of biaryl ketones

Qin

Yasuike

Kakusawa

et al. 2008

Journal of Organometallic Chemistry

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“…Triarylantimony dicarboxylates act as effective arylating agents in Pd-catalyzed C-C(Ar) bond formation reactions such as [28][29][30] 31) and Hiyama-type 32) reactions. Over the past few years, we have also found that they are an efficient aryl donors in base-free Suzuki-type reactions and copper-and base-free Sonogashira-type reactions.…”

Section: The Reaction Of Triarylantimony Diacetates [Ar 3 Sb(oac) 2 ]mentioning

confidence: 99%

Pd-Catalyzed P-Arylation of Triarylantimony Dicarboxylates with Dialkyl H-Phosphites without a Base: Synthesis of Arylphosphonates

Matsumura

Dong

Kakusawa

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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The reaction of triarylantimony diacetates [Ar 3 Sb(OAc) 2 ] with dialkyl H-phosphites [H-PO(OR)2] in the presence of a Pd(PPh 3 ) 4 (5 mol%) catalyst led to the formation of arylphosphonates in moderate to excellent yield under base-free conditions. This reaction is the first example of carbon-phosphorus bond formation by using an organoantimony compound as a pseudo-halide.Key words Hirao-type P-arylation; triarylantimony diacetate; arylphosphonate; dialkyl H-phosphite; basefree reaction Phosphorus-carbon (P-C) bond formation for the synthesis of organophosphorus compounds is a fundamental and significant research topic in organic synthesis, materials, and biology.1-6) Among these, the transition-metal-catalyzed crosscoupling reaction is one of the most practical methods in modern organic syntheses. [7][8][9] With regard to the synthesis of arylphosphonates, the Pd-catalyzed cross-coupling reactions of aryl halides with dialkyl H-phosphites (i.e., Hirao P-arylation) have proved to be a powerful method. [10][11][12][13][14][15][16][17][18][19][20][21] The general procedure of these P-arylations involves a Pd-phosphine complex as the catalyst with the use of a stoichiometric or an excess amount of a base. Recently, different aryl substances were investigated for their reactivity with phosphorus agents. Sulfonates, 22,23) diaryliodonium salts, 24) arylboronic acids, 25) aryldiazonium salts, 26) and triarylbismuthanes 27) have been reported to be useful for P-C bond formation as the arylating reagents with dialkyl H-phosphites; however, a base and/or an additive was required for the transformation.On the other hand, Pd-catalyzed cross-coupling reactions using organoantimony compounds have recently been the focus of attention. Triarylantimony dicarboxylates act as effective arylating agents in Pd-catalyzed C-C(Ar) bond formation reactions such as [28][29][30] 31) and Hiyama-type 32) reactions. Over the past few years, we have also found that they are an efficient aryl donors in base-free Suzuki-type reactions and copper-and base-free Sonogashira-type reactions. [33][34][35] Moreover, base-free Miyaura-type cross-coupling reactions for boron-carbon (B-C) bond formation using triarylantimony diacetates and tetra(alkoxo) diborons afforded the corresponding arylboronates.36) As a continuation of our studies on heteroatom-carbon bond formation, we now report a novel Pd-catalyzed Hirao-type P-arylation of a pentavalent organoantimony compound, triarylantimony diacetate, with dialkyl H-phosphites afford to the corresponding arylphosphonates without using any base. Results and DiscussionWe initially focused our attention on the determination of the optimum conditions for the P-arylation of organoantimony(V) and bismuth(V) compounds (1a-8) with diethyl phosphite (9a) without using a base. The results including the search for active substrates, optimum amount of phosphorus reagent and suitable catalysts for the reaction are summarized in Table 1. The progress of the reaction was monitored by gas-liquid chromatography (GLC) an...

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Pd(0)–Cu(I)-catalyzed cross-coupling of alkynylsilanes with triarylantimony(V) diacetates

Cited by 54 publications

References 17 publications

Sequential and domino Sonogashira coupling: Efficient tools for the synthesis of diarylalkynes

Sequential and domino Sonogashira coupling: Efficient tools for the synthesis of diarylalkynes

Palladium-catalyzed carbonylative cross-coupling reaction of triarylantimony dicarboxylates with arylboronic acids: Synthesis of biaryl ketones

Pd-Catalyzed P-Arylation of Triarylantimony Dicarboxylates with Dialkyl H-Phosphites without a Base: Synthesis of Arylphosphonates

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