scholarly journals Synthesis of Piceatannol, an Oxygenated Analog of Resveratrol

2016 ◽  
Vol 11 (7) ◽  
pp. 1934578X1601100
Author(s):  
Takuya Tashiro ◽  
Shinobu Honzawa ◽  
Takumichi Sugihara
Keyword(s):  
Anticancer Activity ◽  
Red Wine ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Beneficial Effects ◽  
Naturally Occurring ◽  
Cross Coupling Reaction ◽  
Trans Stilbene ◽  
Acid Catalyzed

Piceatannol (3,3′,4,5′-tetrahydroxy- trans-stilbene, 2), an oxygenated analog of resveratrol (1), was synthesized. It is one of the naturally occurring polyphenolic stilbenoids contained in red wine, and possesses many kinds of beneficial effects such as anticancer activity. The trans-stilbene skeleton of 2 was constructed by Pd-catalyzed Suzuki-Miyaura cross coupling reaction of triflate 8 with ( E)-alkenylboronoate 13. The key intermediate 13 was prepared diastereoselectively by acid-catalyzed hydroboration of pinacolborane 12 to alkyne 11.

scholarly journals Total Synthesis of Surinamensinols A and B

SynOpen ◽  
2020 ◽  
Vol 04 (04) ◽  
pp. 84-88
Author(s):  
Ahmed Al-Harrasi ◽  
Satya Kumar Avula ◽  
Biswanath Das ◽  
Rene Csuk ◽  
Ahmed Al-Rawahi
Keyword(s):  
Total Synthesis ◽  
Allyl Alcohol ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Ethyl Lactate ◽  
Naturally Occurring ◽  
Cross Coupling Reaction ◽  
Synthetic Sequence ◽  
Key Steps ◽  
Single Approach

AbstractAn efficient total synthesis of the naturally occurring anti-inflammatory and antitumour 8-O-4′-neolignans, surinamensinols A and B, has been accomplished from commercially available allyl alcohol and (S)-ethyl lactate. The synthetic sequence involves a palladium-catalysed Suzuki–Miyaura cross-coupling reaction followed by a chiral Mitsunobu­ reaction as the key steps. This is the first report of the simultaneous stereoselective total synthesis of surinamensinols A and B through a single approach involving only six steps.

scholarly journals Transition Metal Catalyst Free Cross-Coupling Reaction of Tertiary Propargylic Alcohols with Hetero-Areneboronic Acids

2021 ◽  
Author(s):  
Jian-Fei Bai ◽  
Jianbo Tang ◽  
Xiaolong Gao ◽  
Zhi-Jiang Jiang ◽  
Zhanghua Gao
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Catalyst ◽  
Transition Metal Catalyst ◽  
Propargylic Alcohols ◽  
Catalyst Free ◽  
Cross Coupling Reaction ◽  
Reaction Proceeds ◽  
Acid Catalyzed

We report a perfluorophenylboronic acid catalyzed cross coupling reaction of tertiary propargylic alcohols and hetero-areneboronic acids for valuable benzo[b]thiophene and cyclopenta[a]indene derivates. This coupling reaction proceeds efficiently with a wide array of substrates scope in up to 89% yield and excellent regioselectivity. A significant advantage of our protocol is the transition metal catalyst free and mild conditions needed. This strategy provides direct and facile access to medicinally important benzo[b]thiophene and cyclopenta[a]indene scaffold containing a quaternary carbon center.

scholarly journals Transition Metal Catalyst Free Cross-Coupling Reaction of Tertiary Propargylic Alcohols with Hetero-Areneboronic Acids

2022 ◽  
Author(s):  
Jian-Fei Bai ◽  
Jianbo Tang ◽  
Xiaolong Gao ◽  
Zhi-Jiang Jiang ◽  
Jia Chen ◽  
...  
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Catalyst ◽  
Transition Metal Catalyst ◽  
Propargylic Alcohols ◽  
Catalyst Free ◽  
Cross Coupling Reaction ◽  
Reaction Proceeds ◽  
Acid Catalyzed

We report a perfluorophenylboronic acid catalyzed cross coupling reaction of tertiary propargylic alcohols and hetero-areneboronic acids for valuable benzo[b]thiophene and cyclopenta[a]indene derivates. This coupling reaction proceeds efficiently with a wide array of substrates scope in up to 89% yield and excellent regioselectivity. A significant advantage of our protocol is the transition metal catalyst free and mild conditions needed. This strategy provides direct and facile access to medicinally important benzo[b]thiophene and cyclopenta[a]indene scaffold containing a quaternary carbon center.

Synthesis of a novel series of artemisinin dimers with potent anticancer activity involving Sonogashira cross-coupling reaction

2014 ◽  
Vol 24 (1) ◽  
pp. 237-239 ◽  
Author(s):  
Pori Buragohain ◽  
Bishwajit Saikia ◽  
Naresh Surineni ◽  
Nabin C. Barua ◽  
Ajit K. Saxena ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction

scholarly journals Transition Metal Catalyst Free Cross-Coupling Reaction of Tertiary Propargylic Alcohols with Hetero-Areneboronic Acids

2021 ◽  
Author(s):  
Jian-Fei Bai ◽  
Jianbo Tang ◽  
Xiaolong Gao ◽  
Zhi-Jiang Jiang ◽  
Zhanghua Gao
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Catalyst ◽  
Transition Metal Catalyst ◽  
Propargylic Alcohols ◽  
Catalyst Free ◽  
Cross Coupling Reaction ◽  
Reaction Proceeds ◽  
Acid Catalyzed

We report a perfluorophenylboronic acid catalyzed cross coupling reaction of tertiary propargylic alcohols and hetero-areneboronic acids for valuable benzo[b]thiophene and cyclopenta[a]indene derivates. This coupling reaction proceeds efficiently with a wide array of substrates scope in up to 89% yield and excellent regioselectivity. A significant advantage of our protocol is the transition metal catalyst free and mild conditions needed. This strategy provides direct and facile access to medicinally important benzo[b]thiophene and cyclopenta[a]indene scaffold containing a quaternary carbon center.

Ferromagnetic Chain Based on Verdazyl-Nitroxide Diradical

2020 ◽  
Author(s):  
Evgeny Tretyakov ◽  
Svetlana Zhivetyeva ◽  
Pavel Petunin ◽  
Dmitry Gorbunov ◽  
Nina Gritsan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Ferromagnetic Coupling ◽  
Nitronyl Nitroxide ◽  
Triplet Ground State ◽  
One Dimensional ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Ferromagnetic Chain ◽  
High Yields

<p>Verdazyl-nitroxide diradicals were synthesized using the palladium-catalyzed cross-coupling reaction of the corresponding iodoverdazyls with a nitronyl nitroxide-2-ide gold(I) complex with high yields (up to 82%). The synthesized diradicals were found to be highly thermally stable and have a singlet (D<i>E</i><sub>ST</sub> » -64 cm<sup>–1</sup>) or triplet ground state (D<i>E</i><sub>ST</sub> ³ 25 and 100 cm<sup>–1</sup>), depending on which canonical hydrocarbon diradical type they belong to. Upon crystallization, triplet diradicals form unique one-dimensional (1D) spin <i>S</i> = 1 chains of organic diradicals with intrachain ferromagnetic coupling of <i>J</i>′/<i>k</i><sub>B</sub> from 3 to 6 K.</p>

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

Ni(0)-Catalyzed α-Allylic Alkylation of Regular Ketones with 1,3-Dienes under pH and Redox-neutral Conditions

2019 ◽  
Author(s):  
Tiantian Chen ◽  
Yang Yang ◽  
Liyu Xie ◽  
Haijian Yang ◽  
Guangbin Dong ◽  
...  
Keyword(s):  
Oxidative Addition ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Dual Role ◽  
Allylic Alkylation ◽  
Cross Coupling Reaction ◽  
Neutral Conditions

<p>We report a Ni(0)-catalyzed cross coupling reaction between simple ketones and 1,3-dienes. A variety of a-allylic alkylation products were formed in an 1,2-addition manner with excellent regioselectivity. Water was found to significantly accelerate this transformation. A HO-Ni-H species generated from oxidative addition of Ni(0) to H<sub>2</sub>O is proposed to play a “dual role” in activating both the ketone and the diene substrate.</p>

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