Experimental and Theoretical Study on Palladium-Catalyzed C–P Bond Formation via Direct Coupling of Triarylbismuths with P(O)–H Compounds

Wang, Tao; Sang, Shuai; Liu, Liu; Qiao, Hongwei; Gao, Yuxing; Zhao, Yufen

doi:10.1021/jo402392t

Cited by 76 publications

(31 citation statements)

References 127 publications

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“…The reaction mechanism of the present Sonogashira-type reaction with triarylbismuthanes 1 is unclear at present. We consider that similar mechanisms as in the homo-coupling reaction of triarylbismuthanes proposed by Uemura [27], and P-arylation of dialkyl H-phosphite with triarylbismuthanes under aerobic conditions proposed by Gao [28], as well as the reaction of terminal alkynes with aryl trimethoxysilanes proposed by Cheng [14] and with arylboronic acids as proposed by Bao [11] may be relevant to this reaction demonstrated here. Possible mechanisms for the reaction between terminal alkynes and triarylbismuthanes in the formation of internal alkynes are depicted in Fig.…”

Section: Resultssupporting

confidence: 68%

“…The Pd(0) species is oxidized by the silver cation, and Pd(II) is regenerated. An alternative mechanism path way would involve the generation of Pd(0) species by the reaction of Pd(OAc) 2 with the solvent, substrates and/ or base, followed by the oxidative addition of Ar 3 Bi to the Pd(0) species to give ArPdBi complex (E) [28]. Next, transmetallation with B and reductive elimination would afford the coupling products.…”

Section: Resultsmentioning

confidence: 99%

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Palladium-catalyzed cross-coupling reactions of triarylbismuthanes with terminal alkynes under aerobic conditions

Matsumura

Yamada

Tsuji

et al. 2015

Journal of Organometallic Chemistry

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Section: Resultssupporting

confidence: 68%

Section: Resultsmentioning

confidence: 99%

Palladium-catalyzed cross-coupling reactions of triarylbismuthanes with terminal alkynes under aerobic conditions

Matsumura

Yamada

Tsuji

et al. 2015

Journal of Organometallic Chemistry

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“…A novel and highly efficient cross coupling of triarylbismuths with a variety of H-P¼O compounds was developed [111]. Since the C-Bi bond is week, it easily adds to Pd(0) species in the presence of 2,2 0 -bipyridine (bipy, Fig.…”

Section: Pd-catalyzed Reactionsmentioning

confidence: 99%

“…The catalytic cycle proceeds smoothly without the exclusion of moisture or air, and provides a convenient entry to various arylphosphonates. Some mechanistic aspects of this reaction were probed with DFT calculations [111].…”

Section: Pd-catalyzed Reactionsmentioning

confidence: 99%

Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives

Sobkowski

Kraszewski

Stawiński

2014

Phosphorus Chemistry II

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This chapter provides an overview of recent advances in the development of new methods and protocols for the formation of the P-C bond using H-phosphonate diesters as starting materials. Various chemical and stereochemical aspects of the transition metal-catalyzed cross-coupling and organocatalyst-promoted reactions which are relevant to the synthesis of structurally diverse C-phosphonate derivatives are surveyed.

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“…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.…”

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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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Experimental and Theoretical Study on Palladium-Catalyzed C–P Bond Formation via Direct Coupling of Triarylbismuths with P(O)–H Compounds

Cited by 76 publications

References 127 publications

Palladium-catalyzed cross-coupling reactions of triarylbismuthanes with terminal alkynes under aerobic conditions

Palladium-catalyzed cross-coupling reactions of triarylbismuthanes with terminal alkynes under aerobic conditions

Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives

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

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