Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides

Fu, Tingting; Qiao, Hongwei; Peng, Zhimin; Hu, Guangyuan; Wu, Xueji; Gao, Yuxing; Zhao, Yufen

doi:10.1039/c3ob42470g

Cited by 50 publications

(31 citation statements)

References 59 publications

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“…In a seminal study, Surry et al were able to cross-couple a myriad of secondary phosphines (both alkyl and aryl) with aryl chlorides using the commercially available bidentate phosphine, 1,1′-bis-(diisopropylphosphino)ferrocene (DiPPF), for the palladium catalyst (Scheme 8). Bidentate phosphines are typically required for palladium mediated H-phosphine oxide 48 and H-phosphonate 49 cross-couplings. § This reaction is particularly useful because aryl chlorides are both cheaper and more amenable to late-stage functionalization than aryl bromides.…”

Section: Cross-coupling Trivalent Phosphorusmentioning

confidence: 99%

“…One of the quickly growing subfields in organophosphorus chemistry is the development of H-phosphonate, 48,49,[65][66][67][68][69] H-phosphinate, 70,71 and H-phosphine oxide cross-coupling reactions [72][73][74] to form P-C bonds (Scheme 14). There has been serious interest in these transformations during the last decade and these reactions are now standard practice in organophosphorus synthesis.…”

Section: Cross-coupling Tetravalent Phosphorusmentioning

confidence: 99%

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The synthesis of heteroleptic phosphines

Kendall

Tyler

2015

Dalton Trans.

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Heteroleptic phosphines (R2PR(1)) are a class of essential ligands for inorganic and organometallic chemistry. However, the syntheses of these phosphines are often fraught with laborious synthetic hurdles. Consequently, a renewed interest in innovative synthetic methods to access heteroleptic phosphines is emerging. This Perspective presents an overview of modern synthetic approaches to heteroleptic phosphines as well as a discussion of the strengths and limitations of these synthetic methods. A major emphasis is placed on simple and direct routes to phosphines and significant synthetic innovations for P-C bond-forming reactions.

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Section: Cross-coupling Trivalent Phosphorusmentioning

confidence: 99%

Section: Cross-coupling Tetravalent Phosphorusmentioning

confidence: 99%

The synthesis of heteroleptic phosphines

Kendall

Tyler

2015

Dalton Trans.

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“…Na 2 CO 3 (aq) solution. The organic layer was dried over MgSO 4 , filtered, and evacuated to afford HBndpp 7a as a white solid; yield, 51 mg, 97%; this compound has been previously synthesized via a different method, and NMR data matches that found in the literature: [10] 1H NMR (400 MHz, CDCl3) δ = 7.68 – 7.63 (m, 4H), 7.57 – 7.52 (m, 4H), 7.48 – 7.44 (m, 4H), 7.29 – 7.26 (m, 2H), 2.41 (s, 3H).…”

Section: Methodsmentioning

confidence: 86%

GAP Peptide Synthesis through the Design of a GAP Protecting Group: An Fmoc/tBu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization

et al. 2016

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A novel method for Fmoc/tBu solution-phase peptide synthesis and the development of a new benzyl-type GAP protecting group is reported. This new GAP protecting group is utilized in place of a polymer support, facilitating C→N Fmoc peptide synthesis without chromatography, recrystallization, or polymer supports. The GAP group can be added and removed in high yield, and was used to synthesize over 1 gram of the immunostimulant, thymopentin, in high overall yield (83%) and purity (99%).

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“…Arylboronic acids were reacted with diphenylphosphine oxide, ethyl phenyl- H -phosphinate or diethyl phosphite. The best results were obtained applying the Pd(OAc) 2 -dppb system as the catalyst (Scheme 13 ) [ 139 ].…”

Section: The Traditional Hirao Reactionmentioning

confidence: 99%

New Developments on the Hirao Reactions, Especially from “Green” Point of View

Henyecz

Keglevich

2019

COS

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Background: The Hirao reaction discovered ca. 35 years ago is an important P–C coupling protocol between dialkyl phosphites and aryl halides in the presence of Pd(PPh3)4 as the catalyst and a base to provide aryl phosphonates. Then, the reaction was extended to other Preagents, such as secondary phosphine oxides and H-phosphinates and to other aryl and hetaryl derivatives to afford also phosphinic esters and tertiary phosphine oxides. Instead of the Pd(PPh3)4 catalyst, Pd(OAc)2 and Ni-salts were also applied as catalyst precursors together with a number of mono- and bidentate P-ligands. Objective: In our review, we undertook to summarize the target reaction with a special stress on the developments attained in the last 6 years, hence this paper is an update of our earlier reviews in a similar topic. Conclusion: “Greener” syntheses aimed at utilizing phase transfer catalytic and microwave-assisted approaches, even under “P-ligand-free. or even solvent-free conditions are the up-to date versions of the classical Hirao reaction. The mechanism of the reaction is also in the focus these days.

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Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides

Cited by 50 publications

References 59 publications

The synthesis of heteroleptic phosphines

The synthesis of heteroleptic phosphines

GAP Peptide Synthesis through the Design of a GAP Protecting Group: An Fmoc/tBu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization

New Developments on the Hirao Reactions, Especially from “Green” Point of View

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