Palladium-catalyzed dehydrogenative coupling of terminal alkynes with secondary phosphine oxides

2015 ◽  
Vol 51 (17) ◽  
pp. 3549-3551 ◽  
Author(s):  
Jia Yang ◽  
Tieqiao Chen ◽  
Yongbo Zhou ◽  
Shuangfeng Yin ◽  
Li-Biao Han
Keyword(s):  
Reaction Mechanism ◽  
Palladium Acetate ◽  
Secondary Phosphine ◽  
Terminal Alkynes ◽  
Phosphine Oxides ◽  
Dehydrogenative Coupling ◽  
Palladium Catalyzed ◽  
High Yields

The palladium-catalyzed dehydrogenative coupling of alkynes with secondary phosphine oxides is developed. Thus, in the presence of a silver additive, palladium acetate could efficiently catalyze the dehydrocoupling of secondary phosphine oxides with a variety of alkynes to produce the corresponding alkynylphosphine oxides in high yields. A reaction mechanism is proposed.

Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction

2021 ◽  
Vol 43 (1) ◽  
pp. 95-95
Author(s):  
Rifhat Bibi Rifhat Bibi ◽  
Muhammad Yaseen Muhammad Yaseen ◽  
Haseen Ahmad Haseen Ahmad ◽  
Ismat Ullah Khan Ismat Ullah Khan ◽  
Shaista Parveen Shaista Parveen ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Reaction ◽  
Terminal Alkynes ◽  
Vinyl Halides ◽  
Sonogashira Coupling Reaction ◽  
Quinoxaline Derivatives ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Alkyne Derivatives

Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety of important biological potencies. Palladium catalyzed cross coupling process provided an effective synthetic practice for the synthesis of alkyne derivatives of quinoxaline. Vareity of terminal alkynes were coupled with 2-(4-bromophenyl)quinoxaline under optimized conditions for Sonogashira reaction, affording alkyne substituted quinoxaline derivatives in high yields. The optimized reaction conditions for coupling of range of terminal alkyne with quinoxaline basic core render this process significant for designing of medicinally interesting precursors.

Developing five-membered heterocycle substituted phosphinous acids as ligands for palladium-catalyzed Suzuki–Miyaura and Catellani reactions

2015 ◽  
Vol 44 (39) ◽  
pp. 17129-17142 ◽  
Author(s):  
Ting-Wei Chang ◽  
Pei-Yun Ho ◽  
Kuo-Chung Mao ◽  
Fung-E. Hong
Keyword(s):  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Organic Products ◽  
Palladium Catalyzed ◽  
Membered Heterocycle

Several secondary phosphine oxides (SPOs) were prepared. Organic products with unexpected conformations (9 and 10) were obtained besides 8 from Heck-type Catellani reactions with the assistance of the selected SPO ligand 5f.

An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides

Synthesis ◽  
2019 ◽  
Vol 52 (02) ◽  
pp. 253-262 ◽  
Author(s):  
Teng Liu ◽  
Yanqiong Zhang ◽  
Rong Yu ◽  
Jianjun Liu ◽  
Feixiang Cheng
Keyword(s):  
Atmospheric Oxygen ◽  
Bioactive Molecules ◽  
Practical Approach ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Metal Free ◽  
Dehydrogenative Coupling ◽  
Tetrabutylammonium Iodide

An alternative metal-free, efficient and practical approach for the preparation of phosphinothioates is established via the aerobic oxidative cross-dehydrogenative coupling (CDC) of sulfonyl hydrazides with secondary phosphine oxides catalyzed by tetrabutylammonium iodide (TBAI) in the presence of atmospheric oxygen. The strategy provides an array of diverse phosphinothioates in good to excellent yields. Furthermore, two representative bioactive molecules are synthesized on up to gram scale by utilizing this method.

scholarly journals Secondary Phosphine Oxides as Multitalented Preligands En Route to the Chemoselective Palladium-Catalyzed Oxidation of Alcohols

ChemCatChem ◽  
2017 ◽  
Vol 9 (5) ◽  
pp. 728-732 ◽  
Author(s):  
Alexandre Vasseur ◽  
Romain Membrat ◽  
David Gatineau ◽  
Alphonse Tenaglia ◽  
Didier Nuel ◽  
...  
Keyword(s):  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Oxidation Of Alcohols ◽  
Palladium Catalyzed ◽  
Catalyzed Oxidation

Palladium-Catalyzed C–P Cross-Coupling between (Het)aryl Halides and Secondary Phosphine Oxides

Synthesis ◽  
2019 ◽  
Vol 51 (11) ◽  
pp. 2379-2386 ◽  
Author(s):  
Gladis Zakirova ◽  
Dmitrii Mladentsev ◽  
Nataliya Borisova
Keyword(s):  
Electronic Properties ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Tertiary Phosphine ◽  
Reaction Conditions ◽  
Efficient Procedure ◽  
Palladium Catalyzed ◽  
Tertiary Alkyl

An efficient procedure for C–P bond formation via the palladium-catalyzed [Pd(OAc)2/dppf/Cs2CO3] reaction between dichloroheterocycles and secondary phosphine oxides was developed. The steric and electronic properties of substituents were varied to establish the scope and limitations of the method developed. By applying these conditions, a variety of new heterocyclic compounds bearing two tertiary phosphine oxides were successfully synthesized in moderate to excellent yields. After adjustments to the reaction conditions [Pd(OAc)2/dippf/t-BuOK], cross-coupling of secondary phosphine oxides with bulky (secondary or tertiary alkyl) substituents on the phosphorus atom was achieved. Extension of the methodology to monohalohetarenes and monohaloarenes was successfully carried out; once again, the steric and electronic properties of the halides were varied widely. The desired reaction occurred in all cases studied, giving high to excellent yields of product regardless of the nature and positions of substituents.

Palladium-Catalyzed Dehydrogenative Coupling Reaction of Terminal Alkynes with Unactivated Alkenes

2017 ◽  
Vol 65 (1) ◽  
pp. 117-121 ◽  
Author(s):  
Akira Yada ◽  
Shoki Nishi ◽  
Yuta Sato ◽  
Sakina Ichinoseki ◽  
Masahiro Murakami
Keyword(s):  
Coupling Reaction ◽  
Terminal Alkynes ◽  
Dehydrogenative Coupling ◽  
Palladium Catalyzed

A Novel Access to Tertiary and Secondary ortho-Aminophenylphosphines by Protected Group Synthesis and Palladium Catalyzed P-C Coupling Reactions

2001 ◽  
Vol 56 (4-5) ◽  
pp. 347-353 ◽  
Author(s):  
Antonella Heßler ◽  
Konstantin W. Kottsieper ◽  
Stefan Schenk ◽  
Michael Tepper ◽  
Othmar Stelzer
Keyword(s):  
Coupling Reaction ◽  
Secondary Phosphine ◽  
Coupling Reactions ◽  
The Novel ◽  
Protected Group ◽  
Metallic Lithium ◽  
Subsequent Hydrolysis ◽  
Palladium Catalyzed ◽  
High Yields

Abstract The dilithium salt 1a formed by ortho-metallation of N-tert-butoxycarbonylaniline (BOC-aniline) 1 with two equivalents of tert-butyllithium reacts with the chlorophosphines Ph3-nPCln (n = 1 -3) to yield the BOC protected ortho-aminophenylphosphines 2 - 4 in high yields. On deprotection of 2 - 4 with trimethylchlorosilane in the presence of phenol the HCl adducts of the ortho-aminophenylphosphines 5 -7 are formed which may be deprotonated with KOH or NaOH to give the neutral phosphines 5a -7a. The novel secondary phosphine 8 with two ortho-aminophenyl groups is accessible by cleavage of the P-C bond in 7a with metallic lithium and subsequent hydrolysis. The bifunctional P,N ligands 6 or 6a are alternatively accessible by Pd-catalyzed P-C coupling of ortho-iodoaniline with phenylphosphine. If a 1:1 stoichiometry is employed in the coupling reaction of ortho-iodoaniline and phenylphosphine the chiral secondary phosphine 9 is formed.

Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction

2021 ◽  
Vol 43 (1) ◽  
pp. 95-95
Author(s):  
Rifhat Bibi Rifhat Bibi ◽  
Muhammad Yaseen Muhammad Yaseen ◽  
Haseen Ahmad Haseen Ahmad ◽  
Ismat Ullah Khan Ismat Ullah Khan ◽  
Shaista Parveen Shaista Parveen ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Reaction ◽  
Terminal Alkynes ◽  
Vinyl Halides ◽  
Sonogashira Coupling Reaction ◽  
Quinoxaline Derivatives ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Alkyne Derivatives

Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety of important biological potencies. Palladium catalyzed cross coupling process provided an effective synthetic practice for the synthesis of alkyne derivatives of quinoxaline. Vareity of terminal alkynes were coupled with 2-(4-bromophenyl)quinoxaline under optimized conditions for Sonogashira reaction, affording alkyne substituted quinoxaline derivatives in high yields. The optimized reaction conditions for coupling of range of terminal alkyne with quinoxaline basic core render this process significant for designing of medicinally interesting precursors.

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