d-Glucosamine as an efficient and green additive for palladium-catalyzed Heck reaction

2013 ◽  
Vol 67 (7) ◽  
Author(s):  
Mojtaba Amini ◽  
Hossein Etemadi
Keyword(s):  
Heck Reaction ◽  
Heck Coupling ◽  
Heck Reactions ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
Green Additive

AbstractThe Heck coupling of haloarenes with various alkenes was successfully performed in the presence of 0.5 mole % Pd(OAc)2 and 1.0 mole % d-glucosamine as an additive with K2CO3 as the optimal base in a mixture of H2O/iPrOH (φ r = 2: 1) as the reaction solvent at 80°C after 6 h. d-Glucosamine was found to be an inexpensive, air-stable, easy to available, and efficient additive in palladium-catalyzed Heck reactions of aryl iodides (67–95 % conversion) and bromides (38–72 % conversion).

Palladium-catalyzed Mizoroki–Heck reaction of allyl aryl ethers with aryl iodides using phosphine-free hydrazone ligands

2009 ◽  
Vol 50 (38) ◽  
pp. 5358-5360 ◽  
Author(s):  
Takashi Mino ◽  
Hiroaki Shindo ◽  
Tomoko Kaneda ◽  
Tomoko Koizumi ◽  
Yoshio Kasashima ◽  
...  
Keyword(s):  
Heck Reaction ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
Aryl Ethers ◽  
Hydrazone Ligands

Palladium-Catalyzed Mizoroki-Heck Reaction of Aryl Iodides with Allyl Aryl Ethers Using Imidazo[1, 5-a ]pyridines

2017 ◽  
Vol 2 (31) ◽  
pp. 10143-10145 ◽  
Author(s):  
Fumitoshi Yagishita ◽  
Sota Shimokawa ◽  
Naohiro Uemura ◽  
Yasushi Yoshida ◽  
Takashi Mino ◽  
...  
Keyword(s):  
Heck Reaction ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
Aryl Ethers

Palladium-Catalyzed Heck Reaction of Polyoxometalate-Functionalised Aryl Iodides and Bromides with Olefins

2009 ◽  
Vol 15 (13) ◽  
pp. 3076-3080 ◽  
Author(s):  
Yulin Zhu ◽  
Longsheng Wang ◽  
Jian Hao ◽  
Panchao Yin ◽  
Jin Zhang ◽  
...  
Keyword(s):  
Heck Reaction ◽  
Aryl Iodides ◽  
Palladium Catalyzed

Practical Intermolecular Hydroarylation of Terminal Alkenes via Reductive Heck Coupling

2018 ◽  
Author(s):  
John A. Gurak ◽  
Keary M. Engle
Keyword(s):  
Functional Groups ◽  
Complex Molecule ◽  
Reductive Elimination ◽  
Heck Coupling ◽  
Deuterium Labeling ◽  
Aryl Iodides ◽  
Terminal Alkenes ◽  
Palladium Catalyzed ◽  
Turn Over

The hydroarylation of alkenes is an attractive approach to construct carbon–carbon (C–C) bonds from abundant and structurally diverse starting materials. Herein we report a palladium-catalyzed reductive Heck hydroarylation of unactivated and heteroatom-substituted terminal alkenes with an array of (hetero)aryl iodides. The reaction is anti-Markovnikov selective and tolerates a wide variety of functional groups on both the alkene and (hetero)aryl coupling partners. Additionally, applications of this method to complex molecule diversifications were demonstrated. Deuterium-labeling experiments are consistent with a mechanism in which the key alkylpalladium(II) intermediate is intercepted with formate and undergoes a decarboxylation/C–H reductive elimination cascade to afford the saturated product and turn over the cycle. <br>

Palladium-Catalyzed Regioselective Heck Coupling of Alkynes with Aryl Iodides for the Synthesis of Trisubstituted Allenes

2019 ◽  
Vol 21 (19) ◽  
pp. 7795-7798 ◽  
Author(s):  
Weiwei Lv ◽  
Yanhui Chen ◽  
Zemin Zhao ◽  
Si Wen ◽  
Guolin Cheng
Keyword(s):  
Heck Coupling ◽  
Aryl Iodides ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Mizoroki—Heck Reaction of Allyl Aryl Ethers with Aryl Iodides Using Phosphine-Free Hydrazone Ligands.

ChemInform ◽  
2009 ◽  
Vol 40 (51) ◽  
pp. no-no
Author(s):  
Takashi Mino ◽  
Hiroaki Shindo ◽  
Tomoko Kaneda ◽  
Tomoko Koizumi ◽  
Yoshio Kasashima ◽  
...  
Keyword(s):  
Heck Reaction ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
Aryl Ethers ◽  
Hydrazone Ligands
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