scholarly journals Palladium catalyzed regioselective B–C(sp) coupling via direct cage B–H activation: synthesis of B(4)-alkynylated o-carboranes

2016 ◽  
Vol 7 (9) ◽  
pp. 5838-5845 ◽  
Author(s):  
Yangjian Quan ◽  
Cen Tang ◽  
Zuowei Xie
Keyword(s):  
Terminal Alkynes ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
First Time ◽  
Intermolecular Coupling

Palladium-catalyzed direct intermolecular coupling of o-carboranes with alkynyl bromides or terminal alkynes has been achieved, for the first time, with the help of a traceless directing group –COOH, leading to the synthesis of a series of new cage B(4)-alkynylated-o-carboranes in high yields with excellent regioselectivity.

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

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.

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.

scholarly journals A dual role for acetohydrazide in Pd-catalyzed controlled C(sp3)–H acetoxylation of aldehydes

RSC Advances ◽  
2020 ◽  
Vol 10 (21) ◽  
pp. 12192-12196
Author(s):  
Juan Chen ◽  
Chaolumen Bai ◽  
XingWen Tong ◽  
Dan Liu ◽  
Yong-Sheng Bao
Keyword(s):  
Dual Role ◽  
Group Approach ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
First Time

The palladium catalyzed aldehyde directed acetoxylation of C(sp3)–H bonds was realized by a transient directing group approach for the first time.

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.

Synthesis of new porphyrin dimers linked by diamines and their supramolecular assemblies

2015 ◽  
Vol 19 (07) ◽  
pp. 874-886 ◽  
Author(s):  
Elena A. Mikhalitsyna ◽  
Vladimir S. Tyurin ◽  
Irina P. Beletskaya
Keyword(s):  
Supramolecular Assembly ◽  
Copper Cation ◽  
Supramolecular Assemblies ◽  
Amination Reaction ◽  
Vis Spectroscopy ◽  
Palladium Catalyzed ◽  
High Yields ◽  
First Time ◽  
Porphyrin Dimers

For the first time the bisporphyrins connected via diamine bridges were synthesized by palladium catalyzed Buchwald–Hartwig amination reaction with high yields. The diamine bridges include linear, cyclic and macrocyclic types. Homo- and heteronuclear metallocomplexes of bisporphyrins were investigated with UV-vis spectroscopy in the processes of supramolecular assembly. The interaction with diazabicyclo[2.2.2]octane (DABCO) and cesium and diammonium cations led to the coordination dimers. Control of the conformation of the bisporphyrin was realized via coordination of diamine moiety with copper cation.

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

Nickel-Catalyzed Annulation of Aliphatic Amides with Alkynyl­silanes: An Expeditious Approach to Five-Membered Lactams

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 889-894
Author(s):  
Cong Lin ◽  
Liang Shen ◽  
Yiqing Xu ◽  
Qiuxun Teng ◽  
Jingyi Lin ◽  
...  
Keyword(s):  
Transition Metal ◽  
Directing Group ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
High Yields ◽  
First Time

An expeditious approach for the synthesis of diverse five-membered lactams through nickel-catalyzed annulation of the C(sp3)–H bonds of aliphatic amides with alkynylsilanes assisted by an 8-aminoquinolinyl directing group is reported, delivering the corresponding lactam derivatives in moderate to high yields. It is worth noting that alkynylsilanes are employed for the first time as coupling partners in the transition-metal-catalyzed functionalization of C(sp3)–H bonds of aliphatic amides. Equimolar amounts of alkynylsilanes and aliphatic amides are utilized, which greatly increases the efficiency of this protocol.

Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether

2017 ◽  
Vol 53 (27) ◽  
pp. 3894-3897 ◽  
Author(s):  
Madala Hari Babu ◽  
Gadi Ranjith Kumar ◽  
Ruchir Kant ◽  
Maddi Sridhar Reddy
Keyword(s):  
Catalytic System ◽  
Terminal Alkynes ◽  
Arylboronic Acids ◽  
Stereoselective Addition ◽  
Directing Group ◽  
First Time ◽  
P Addition

Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units.

Palladium-catalyzed directing group-assisted C8-triflation of naphthalenes

2016 ◽  
Vol 52 (40) ◽  
pp. 6709-6711 ◽  
Author(s):  
Zhi-Wei Yang ◽  
Qi Zhang ◽  
Yuan-Ye Jiang ◽  
Lei Li ◽  
Bin Xiao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
First Time

The transition-metal-catalyzed direct triflation of naphthyl amides and naphthyl ketones has been accomplished for the first time.

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