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>

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-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.

Visible-Light-Induced Palladium-Catalyzed Intermolecular Narasaka–Heck Reaction at Room Temperature

2020 ◽  
Vol 22 (10) ◽  
pp. 3964-3968 ◽  
Author(s):  
Liyan Feng ◽  
Lin Guo ◽  
Chao Yang ◽  
Jia Zhou ◽  
Wujiong Xia
Keyword(s):  
Visible Light ◽  
Heck Reaction ◽  
Room Temperature ◽  
Palladium Catalyzed

Blue Light Enhanced Heck Arylation at Room Temperature Applied to Allenes

2022 ◽  
Author(s):  
Polyssena Renzi ◽  
Emanuele Azzi ◽  
Enrico Bessone ◽  
Giovanni Ghigo ◽  
Stefano Parisotto ◽  
...  
Keyword(s):  
Visible Light ◽  
Blue Light ◽  
Catalytic System ◽  
Heck Reaction ◽  
Room Temperature ◽  
Aryl Halides ◽  
Heck Arylation

An unprecedented visible light enhanced room temperature Heck reaction between aryl halides and allenyl tosyl amines is here reported. The simple catalytic system (Pd(OAc)2/PPh3) is exploited to afford arylated vinyl...

Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene derivatives for C(sp3)–C(sp) bond formation catalyzed by a B12 complex

2019 ◽  
Vol 55 (87) ◽  
pp. 13070-13073 ◽  
Author(s):  
Li Chen ◽  
Yohei Kametani ◽  
Kenji Imamura ◽  
Tsukasa Abe ◽  
Yoshihito Shiota ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Bond Formation ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Visible Light Driven

Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene and its derivatives catalyzed by the cobalamin derivative (B12) with the [Ir(dtbbpy)(ppy)2]PF6 photocatalyst at room temperature are reported.

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
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