Radical C(sp3)–H alkenylation, alkynylation and allylation of ethers and amides enabled by photocatalysis

2017 ◽  
Vol 19 (11) ◽  
pp. 2530-2534 ◽  
Author(s):  
Subhasis Paul ◽  
Joyram Guin
Keyword(s):  
Good Yield ◽  
Radical Addition ◽  
Elimination Reaction

A photocatalytic radical addition/elimination reaction that enables direct C(sp3)–H alkenylation, alkynylation and allylation of ethers/amides with good yield and stereoselectivity.

Development of radical addition–cyclization–elimination reaction of oxime ether and its application to formal synthesis of (±)-martinelline

Tetrahedron ◽  
2007 ◽  
Vol 63 (40) ◽  
pp. 10092-10117 ◽  
Author(s):  
Okiko Miyata ◽  
Atsushi Shirai ◽  
Shintaro Yoshino ◽  
Toshiki Nakabayashi ◽  
Yoshifumi Takeda ◽  
...  
Keyword(s):  
Radical Addition ◽  
Elimination Reaction ◽  
Oxime Ether ◽  
Formal Synthesis

An ionic chain mechanism for the substitution of an acetate group by the 2-Nitropropan-2-ide ion in benzylidene diacetates

1976 ◽  
Vol 29 (2) ◽  
pp. 327 ◽  
Author(s):  
DJ Freeman ◽  
PJ Newcombe ◽  
RK Norris
Keyword(s):  
Good Yield ◽  
Dimethyl Sulphoxide ◽  
Acetate Group ◽  
Chain Mechanism ◽  
Elimination Reaction ◽  
Nucleophilic Cleavage ◽  
Enol Acetates ◽  
Subsequent Elimination

The reaction of 16 arylmethylene diacetates [benzylidene diacetates; ArCH(OAc)2] with lithium 2-nitropropan-2-ide in dimethyl sulphoxide has been studied. With the exception of aryl rings bearing strongly electron-donating substituents a ready reaction takes place giving l-aryl-2-methyl-2-nitropropyl acetates in good yield. The mechanism of this reaction, in which an acetate group is formally substituted by a (CH3)2C(N02) group, has been shown to be an ionic chain mechanisminvolving nucleophilic cleavage of the diacetate to catalytic quantities of the corresponding arene carbaldehyde (ArCHO) which subsequently undergoes a Henry condensation followed by a transacetylation reaction. In some cases (nitro heteroaromatic derivatives) a subsequent elimination reaction gives enol-acetates [ArC(OAc)=C(CH3)2].

Total Synthesis of (−)-Martinellic Acid via Radical Addition−Cyclization−Elimination Reaction

2008 ◽  
Vol 73 (12) ◽  
pp. 4464-4475 ◽  
Author(s):  
Atsushi Shirai ◽  
Okiko Miyata ◽  
Norimitsu Tohnai ◽  
Mikiji Miyata ◽  
David J. Procter ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Radical Addition ◽  
Elimination Reaction ◽  
Martinellic Acid

Scope of the radical addition–cyclization–elimination reaction of oxime ether towards the synthesis of tricyclic lactam derivatives

2008 ◽  
Vol 49 (40) ◽  
pp. 5789-5792 ◽  
Author(s):  
Habibur Rahaman ◽  
Atsushi Shirai ◽  
Okiko Miyata ◽  
Takeaki Naito
Keyword(s):  
Radical Addition ◽  
Elimination Reaction ◽  
Oxime Ether
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