- Copper-Catalyzed Dehydrogenative Diels-Alder Reaction
-
A practical and effective copper-catalyzed dehydrogenative Diels-Alder reaction of gem-diesters and ketone with dienes has been established. The active dienophiles were generated in situ via a radical-based dehydrogenation process, which reacted with a wide variety of dienes to afford various polysubstituted cyclohexene derivatives in good to excellent yields.
- Jiang, Bing,Liang, Qiu-Ju,Han, Yu,Zhao, Meng,Xu, Yun-He,Loh, Teck-Peng
-
p. 3215 - 3219
(2018/06/11)
-
- Solid Acid-Catalyzed Dehydration of Pinacol Derivatives in Ionic Liquid: Simple and Efficient Access to Branched 1,3-Dienes
-
The selective dehydration of pinacol derivatives to branched 1,3-dienes is extremely challenging because of the predominance of pinacol rearrangement. Herein, we successfully achieve this goal by employing a recyclable solid acid/ionic liquid catalyst system. The dehydration of alkyl- and cycloalkyl-derived diols in an Amberlyst-15/[Emim]Cl system afforded the corresponding 1,3-dienes in good yields, while a Nafion/[Emim]Cl system was demonstrated to be a better catalyst system for the dehydration of aryl-substituted substrates. Our protocol features straightforward and simple access to branched 1,3-dienes, high chemoselectivity, a recyclable catalyst system, a facile separation of dienes just by decantation, and a broad substrate scope.
- Hu, Yancheng,Li, Ning,Li, Guangyi,Wang, Aiqin,Cong, Yu,Wang, Xiaodong,Zhang, Tao
-
p. 2576 - 2582
(2017/05/31)
-
- From propargylic biscarbonate to diaryl[n]dendralenes
-
An efficient cross-coupling reaction using a low cost carbon-supported palladium (Pd/C) catalyst for the synthesis of cross-conjugated compounds, diaryl[n]dendralenes, has been developed. The reaction of a propargylic biscarbonate with phenylboronic acid using Pd/C and phosphine ligand (S-Phos) gave 2,3-diphenyl[2]dendralene in high yield. We found that Pd/C was an effective catalyst for the synthesis of dialyl[n]dendralenes. The synthesis of various dendralenes was successfully achieved under the optimized conditions, giving dialyl [2] and [4] dendralenes in good yields.
- Hayashi, Shotaro,Kasuya, Masakatsu,Machida, Junsuke,Koizumi, Toshio
-
p. 2429 - 2432
(2017/06/01)
-
- Facile synthesis of dibranched conjugated dienes via palladium-catalyzed oxidative coupling of N-tosylhydrazones
-
A facile and highly regioselective Pd-catalyzed oxidative coupling of N-tosylhydrazones providing efficient access to 2,3-disubstituted-1,3-butadienes has been developed. This process features readily available starting materials and mild reaction conditions. Further transformations of the obtained dibranched 1,3-dienes, through Diels-Alder reactions and indene synthesis, are also demonstrated, which reveal their great potential for synthetic utility.
- Jiang, Huanfeng,He, Li,Li, Xianwei,Chen, Huoji,Wu, Wanqing,Fu, Wei
-
supporting information
p. 9218 - 9220
(2013/09/24)
-
- Synthesis of indenes via Bronsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes
-
Substituted indenes can be synthesized via the Bronsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes. In this approach, treatment of symmetric or unsymmetric diaryl- and alkyl aryl-1,3-dienes with a catalytic amount of trifluoromethanesulfonic acid gives a variety of indene derivatives in good to excellent yields under mild conditions.
- Eom, Dahan,Park, Sangjune,Park, Youngchul,Ryu, Taekyu,Lee, Phil Ho
-
supporting information
p. 5392 - 5395,4
(2012/12/12)
-
- Synthesis of indenes via Br?nsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes
-
Substituted indenes can be synthesized via the Br?nsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes. In this approach, treatment of symmetric or unsymmetric diaryl- and alkyl aryl-1,3-dienes with a catalytic amount of trifluoromethanesulfonic acid gives a variety of indene derivatives in good to excellent yields under mild conditions.
- Eom, Dahan,Park, Sangjune,Park, Youngchul,Ryu, Taekyu,Lee, Phil Ho
-
supporting information
p. 5392 - 5395
(2013/01/15)
-
- Direct one-pot synthesis of 2,3-diarylbuta-1,3-diene via self-coupling of acetophenones
-
A mild and straightforward route to 2,3-diarylbuta-1,3-diene is described here. By treatment with SmI2-Ac20, acetophe-none and its analogues underwent self-coupling reactions and subsequent elimination to give a series of 2,3-diarylbuta-1,3-dienes in moderate to good yields.
- Li, Jian,Li, Shaoyu,Jia, Xueshun
-
experimental part
p. 1529 - 1531
(2009/04/07)
-
- SYNTHESES WITH DIKETO SELENIDES
-
We report a) a modified synthesis of diketo selenides, b) preparation of 2,5-diacylselenophenes by condensation of diketoselenides with glyoxal, c) preparation of poly-substituted selenophenes by intramolecular reductive coupling reaction of diketo selenides with low-valent titanium reagent under controlled conditions (0 degC) followed by dehydratation of the resulting 3,4-dihydroxyselenolanes, and d) formation of 2,5-dihydroselenophenes and 1,3-dienes by treatment of diketo selenides with the low-valent titanium reagent in refluxing tetrahydrofuran.
- Nakayama, Juzo,Shibuya, Masahiro,Ikuina, Yoji,Murai, Fumito,Hoshino, Masamatsu
-
p. 149 - 156
(2007/10/02)
-
- Formation of 2,5-Dihydroselenophenes and 1,3-Dienes from Diketo Selenides by Reduction with Low-valent Titanium Reagents
-
Reduction of a series of diketo selenides with a low-valent titanium reagent affords 2,5-dihydroselenophenes and 1,3-dienes in comparable yields.
- Nakayama, Juzo,Ikuina, Yoji,Murai, Fumito,Hoshino, Masamatsu
-
p. 1072 - 1073
(2007/10/02)
-
- NOVEL SYNTHESIS OF 2,3-DIARYLBUTA-1,3-DIENES FROM 1,4-DIMETHOXYBUTYNE-2
-
It was found that 2,3-diarylbuta-1,3-dienes were readily obtained in good to excellent yields through the SN-2' type substitution of 1,4-dimethoxybutyne-2 with aryl Grignard reagents in the presence of a copper(I) salt.
- Ishino, Yoshio,Nishiguchi, Ikuzo,Takihira, Fujio,Hirashima, Tsuneaki
-
p. 1527 - 1528
(2007/10/02)
-