Metal-free oxidative decarbonylative alkylation of chromones using aliphatic aldehydes

2018 ◽  
Vol 16 (19) ◽  
pp. 3568-3571 ◽  
Author(s):  
Rongzhen Chen ◽  
Jin-Tao Yu ◽  
Jiang Cheng
Keyword(s):  
Conjugate Addition ◽  
Aliphatic Aldehydes ◽  
Metal Free ◽  
Alkylating Reagents

A decarbonylative alkylation of chromones via radical conjugate addition under metal-free conditions was developed using aliphatic aldehydes as alkylating reagents.

Enantioselective Preparation of Alcohols and Amines:The Suh Synthesis of (-)-Macrosphelide J

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Conjugate Addition ◽  
Aliphatic Aldehyde ◽  
Geometric Control ◽  
Cinchona Alkaloid ◽  
University Of Virginia ◽  
Aliphatic Aldehydes ◽  
Salen Complex ◽  
Complementary Approach ◽  
National University ◽  
The University

Keiji Maruoka of Kyoto University (J. Am. Chem. Soc. 2009, 131, 3450) and Yujiro Hayashi of the Tokyo University of Science (Chem. Commun. 2009, 3083) independently developed organocatalysts for the enantioselective α-benzoylation of aliphatic aldehydes such as 1. The product 3 can be readily carried on to, inter alia, either enantiomer of the epoxide. Chengjian Zhu of Nanjing University designed (Adv. Synth. Cat. 2009, 351, 920) a chiral salen complex that mediated the enantioselective opening of both cyclohexene oxide (4) and cyclopentene oxide. This reagent combination might also engage just one of the two enantiomers of a racemic cycloalkene epoxide. Lin Pu of the University of Virginia established (Organic Lett. 2009, 11, 2441) a BINOL catalyst for the addition of ethyl propiolate 7 to an aliphatic aldehyde 6 to give the alcohol 8 in high ee. In a complementary approach, Do Hyun Ryu of Sungkyunkwan University found (Angew. Chem. Int. Ed. 2009, 48, 4398) that an oxazaborolidinium salt catalyzed the addition of 7 to 9 to give 10 with high ee and high geometric control. Jianliang Xiao of the University of Liverpool devised (J. Am. Chem. Soc. 2009, 131, 6967) an Ir catalyst for the enantioselective reductive amination of a ketone 11 to the amine 13 . Karl B. Hansen, Yi Hsiao. and Feng Xu, then all at Merck/Rahway, showed (J. Am. Chem. Soc. 2009, 131, 8798) that it was possible to hydrogenate a vinylogous primary amide 14 to the amine 15 with high enantiocontrol. Takashi Ooi of Nagoya University designed (J. Am. Chem. Soc. 2009, 131, 7242) a chiral P-spiro tetraaminophosphonium catalyst that mediated the enantioselective addition of anilines to nitroalkenes such as 16. The product 18 could be carried on to the 1,2-diamine, or to the α-amino acid. Masahiro Terada of Tohoku University devised (Angew. Chem. Int. Ed. 2009, 48, 2553) a BINOL-derived phosphonic acid to catalyze the enantioselective 1,2-addition of the enamide 20 to the imine derived from 19. Yixin Lu of the National University of Singapore found (Organic Lett. 2009, 11, 1721) that a cinchona alkaloid-derived thiourea effectively catalyzed the enantioselective conjugate addition of nitroalkanes such as 22 to the acceptor 23.

Conjugate addition from the excited state

2018 ◽  
Vol 54 (78) ◽  
pp. 11021-11024 ◽  
Author(s):  
Akila Iyer ◽  
Sapna Ahuja ◽  
Steffen Jockusch ◽  
Angel Ugrinov ◽  
Jayaraman Sivaguru
Keyword(s):  
Excited State ◽  
Visible Light ◽  
Conjugate Addition ◽  
Metal Free

Conjugate addition occurs efficiently from excited hydrazide based acrylanilides under both UV and metal free visible light irradiations.

1,2-Arylalkylation of N-(arylsulfonyl)acrylamides using aliphatic aldehydes as the alkyl source

2017 ◽  
Vol 15 (26) ◽  
pp. 5476-5479 ◽  
Author(s):  
Jin-Tao Yu ◽  
Rongzhen Chen ◽  
Jiawei Zhu ◽  
Jiang Cheng
Keyword(s):  
Alkyl Radical ◽  
Aliphatic Aldehydes ◽  
Metal Free

A metal-free decarbonylative arylalkylation of N-(arylsulfonyl)acrylamides using aliphatic aldehydes as the alkyl radical source was developed.

Transition-Metal-Free Quinoline Synthesis from Acetophenones and Anthranils via Sequential One-Carbon Homologation/Conjugate Addition/Annulation Cascade

2017 ◽  
Vol 19 (18) ◽  
pp. 4948-4951 ◽  
Author(s):  
Sandip Balasaheb Wakade ◽  
Dipak Kumar Tiwari ◽  
Pothapragada S. K. Prabhakar Ganesh ◽  
Mandalaparthi Phanindrudu ◽  
Pravin R. Likhar ◽  
...  
Keyword(s):  
Transition Metal ◽  
Conjugate Addition ◽  
Metal Free

Metal-free cascade oxidative decarbonylative alkylarylation of acrylamides with aliphatic aldehydes: a convenient approach to oxindoles via dual C(sp2)–H bond functionalization

2016 ◽  
Vol 18 (10) ◽  
pp. 2941-2945 ◽  
Author(s):  
Luo Yang ◽  
Wen Lu ◽  
Wang Zhou ◽  
Feng Zhang
Keyword(s):  
Aliphatic Aldehydes ◽  
Bond Functionalization ◽  
Metal Free ◽  
Convenient Approach

A convenient metal-free cascade oxidative decarbonylative alkylarylation of acrylamides with aliphatic aldehydes to provide quaternary oxindoles is developed.

Aliphatic Aldehydes: Novel Radical Alkylating Reagents

2019 ◽  
Vol 361 (8) ◽  
pp. 1700-1709 ◽  
Author(s):  
Wen‐Chao Yang ◽  
Jian‐Guo Feng ◽  
Lei Wu ◽  
Yong‐Qiang Zhang
Keyword(s):  
Aliphatic Aldehydes ◽  
Alkylating Reagents
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