Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature

2017 ◽  
Vol 139 (50) ◽  
pp. 18307-18312 ◽  
Author(s):  
Guang-Zu Wang ◽  
Rui Shang ◽  
Wan-Min Cheng ◽  
Yao Fu
Keyword(s):  
Heck Reaction ◽  
Room Temperature ◽  
Alkyl Halides

Aliphatic Radical Relay Heck Reaction at Unactivated C(sp3)–H Sites of Alcohols

2018 ◽  
Author(s):  
Padon Chuentragool ◽  
Dongari Yadagiri ◽  
Taiki Morita ◽  
Sumon Sarkar ◽  
Marvin Parasram ◽  
...  
Keyword(s):  
Visible Light ◽  
Heck Reaction ◽  
Room Temperature ◽  
Halogen Atom ◽  
Organic Molecules ◽  
Alkyl Halides ◽  
Aliphatic Alcohols ◽  
Aliphatic Radical ◽  
Reaction Proceeds

<div>The Mizoroki−Heck reaction is one of the most efficient methods for alkenylation of</div><div>aryl, vinyl, and alkyl halides. Due to its innate nature, this protocol requires the employment of compounds possessing a halogen atom at the site of functionalization. However, the accessibility of organic molecules possessing a halogen atom at a particular site in aliphatic systems is extremely limited. Thus, a protocol that would allow a Heck reaction to occur at a specific non-functionalized C(sp3)−H site would be highly desirable.</div><div>Here, we report a radical relay Heck reaction which allows for a selective remote</div>alkenylation of aliphatic alcohols at unactivated β-, γ- and δ-C(sp3 20 )–H sites. The use of easily installable/removable Si-based auxiliary enables selective I-atom/radical translocation events at remote C−H sites followed by the Heck reaction. Notably, the reaction proceeds smoothly under mild visible light-mediated conditions at room temperature, producing highly modifiable and valuable alkenol products from readily available alcohols feedstocks. <br>

scholarly journals Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes

2017 ◽  
Vol 129 (45) ◽  
pp. 14400-14404 ◽  
Author(s):  
Daria Kurandina ◽  
Marvin Parasram ◽  
Vladimir Gevorgyan
Keyword(s):  
Visible Light ◽  
Heck Reaction ◽  
Room Temperature ◽  
Alkyl Halides

Aliphatic Radical Relay Heck Reaction at Unactivated C(sp3)–H Sites of Alcohols

2018 ◽  
Author(s):  
Padon Chuentragool ◽  
Dongari Yadagiri ◽  
Taiki Morita ◽  
Sumon Sarkar ◽  
Marvin Parasram ◽  
...  
Keyword(s):  
Visible Light ◽  
Heck Reaction ◽  
Room Temperature ◽  
Halogen Atom ◽  
Organic Molecules ◽  
Alkyl Halides ◽  
Aliphatic Alcohols ◽  
Aliphatic Radical ◽  
Reaction Proceeds

<div>The Mizoroki−Heck reaction is one of the most efficient methods for alkenylation of</div><div>aryl, vinyl, and alkyl halides. Due to its innate nature, this protocol requires the employment of compounds possessing a halogen atom at the site of functionalization. However, the accessibility of organic molecules possessing a halogen atom at a particular site in aliphatic systems is extremely limited. Thus, a protocol that would allow a Heck reaction to occur at a specific non-functionalized C(sp3)−H site would be highly desirable.</div><div>Here, we report a radical relay Heck reaction which allows for a selective remote</div>alkenylation of aliphatic alcohols at unactivated β-, γ- and δ-C(sp3 20 )–H sites. The use of easily installable/removable Si-based auxiliary enables selective I-atom/radical translocation events at remote C−H sites followed by the Heck reaction. Notably, the reaction proceeds smoothly under mild visible light-mediated conditions at room temperature, producing highly modifiable and valuable alkenol products from readily available alcohols feedstocks. <br>

scholarly journals Dehalogenation of functionalized alkyl halides in water at room temperature

2015 ◽  
Vol 17 (2) ◽  
pp. 893-897 ◽  
Author(s):  
Nicholas A. Isley ◽  
Matt S. Hageman ◽  
Bruce H. Lipshutz
Keyword(s):  
Room Temperature ◽  
Alkyl Halides ◽  
Alkyl Bromides ◽  
Green Conditions

Alkyl bromides and chlorides can be reduced to the corresponding hydrocarbons utilizing zinc in the presence of an amine additive under very mild, green conditions.

ChemInform Abstract: Cross-Coupling of Alkyl Halides with Heteroaromatic Halides, in Water at Room Temperature.

ChemInform ◽  
2011 ◽  
Vol 42 (30) ◽  
pp. no-no
Author(s):  
Arkady Krasovskiy ◽  
Isabelle Thome ◽  
Julien Graff ◽  
Valeria Krasovskaya ◽  
Paul Konopelski ◽  
...  
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Alkyl Halides

scholarly journals Enhancing the reactivity of 1,2-diphospholes in cycloaddition reactions

2015 ◽  
Vol 11 ◽  
pp. 169-173 ◽  
Author(s):  
Almaz Zagidullin ◽  
Vasili Miluykov ◽  
Elena Oshchepkova ◽  
Artem Tufatullin ◽  
Olga Kataeva ◽  
...  
Keyword(s):  
Room Temperature ◽  
Cycloaddition Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Alkyl Halides ◽  
Ethyl Iodide ◽  
Para Position ◽  
Cycloaddition Reactions ◽  
Diels Alder Reaction ◽  
Heating Up

Two different approaches have been employed to enhance the reactivity of 1-alkyl-1,2-diphospholes – the introduction of electron-withdrawing groups either at the phosphorus atoms or in the para-position of the arene ring. The alkylation of sodium 1,2-diphospha-3,4,5-triphenylcyclopentadienide with alkyl halides Hal-CH2-R (R = CN, COOEt, OMe, CH2OEt) results in corresponding 1-alkyl-3,4,5-triphenyl-1,2-diphospholes (alkyl = CH2CN (1a), CH2COOEt (1b), CH2OMe (1c), and (CH2)2OEt (1d)), which spontaneously undergo the intermolecular [4 + 2] cycloaddition reactions at room temperature to form the mixture of the cycloadducts, 2a–c, respectively. However the alkylation of sodium 1,2-diphospha-3,4,5-tri(p-fluorophenyl)cyclopentadienide with ethyl iodide leads to stable 1-ethyl-3,4,5-tris(p-fluorophenyl)-1,2-diphosphole (1e), which forms the [4 + 2] cycloadduct 2,3,4,4a,5,6-hexa(p-fluorophenyl)-1-ethyl-1,7,7a-triphospha-4,7-(ethylphosphinidene)indene (2e) only upon heating up to 60 °C. With further heating to 120 °C with N-phenylmaleimide, the cycloadducts 2a–c and 2e undergo the retro-Diels–Alder reaction and form only one product of the [4 + 2] cycloaddition reaction 3a–с, 3e with good yields up to 65%.

ChemInform Abstract: Photoinduced, Copper-Catalyzed Alkylation of Amides with Unactivated Secondary Alkyl Halides at Room Temperature.

ChemInform ◽  
2014 ◽  
Vol 45 (34) ◽  
pp. no-no
Author(s):  
Hien-Quang Do ◽  
Shoshana Bachman ◽  
Alex C. Bissember ◽  
Jonas C. Peters ◽  
Gregory C. Fu
Keyword(s):  
Room Temperature ◽  
Alkyl Halides

scholarly journals Heck Reaction of Electronically Diverse Tertiary Alkyl Halides

2018 ◽  
Vol 20 (2) ◽  
pp. 357-360 ◽  
Author(s):  
Daria Kurandina ◽  
Mónica Rivas ◽  
Maxim Radzhabov ◽  
Vladimir Gevorgyan
Keyword(s):  
Heck Reaction ◽  
Alkyl Halides ◽  
Tertiary Alkyl

scholarly journals Visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using O2 as an oxidant

2019 ◽  
Vol 10 (4) ◽  
pp. 976-982 ◽  
Author(s):  
Jianyang Dong ◽  
Xueli Lyu ◽  
Zhen Wang ◽  
Xiaochen Wang ◽  
Hongjian Song ◽  
...  
Keyword(s):  
Visible Light ◽  
Molecular Oxygen ◽  
Room Temperature ◽  
Alkyl Halides

Herein, we report a protocol for direct visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using molecular oxygen as an oxidant at room temperature.

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