2619-00-3Relevant academic research and scientific papers
Room-temperature Pd-catalyzed C-H chlorination by weak coordination: One-pot synthesis of 2-chlorophenols with excellent regioselectivity
Sun, Xiuyun,Sun, Yonghui,Zhang, Chao,Rao, Yu
supporting information, p. 1262 - 1264 (2014/02/14)
A room-temperature Pd(ii)-catalyzed regioselective chlorination reaction has been developed for a facile one-pot synthesis of a broad range of 2-chlorophenols. The reaction demonstrates an excellent regioselectivity and reactivity for C-H chlorination. This reaction represents one of the rare examples of mild C-H functionalization at ambient temperature.
A general approach towards catechol and pyrogallol through ruthenium- and palladium-catalyzed C-H hydroxylation by weak coordination
Yang, Xinglin,Sun, Yonghui,Chen, Zhang,Rao, Yu
supporting information, p. 1625 - 1630 (2014/06/09)
An efficient ruthenium(II)- and palladium(II)-catalyzed C-H hydroxylation of aryl carbamates has been developed for the facile synthesis of catechols and pyrogallols. The reaction demonstrates excellent reactivity, regio- and chemoselectivity, good functional group compatibility and high yields. The practicality of this method has been proved by a gram-scale synthesis.
Microwave-promoted copper-free Sonogashira-Hagihara couplings of aryl imidazolylsulfonates in water
Civicos, Jose F.,Alonso, Diego A.,Najera, Carmen
supporting information, p. 203 - 208 (2013/03/14)
Aryl imidazol-1-ylsulfonates have been efficiently cross-coupled with aryl-, alkyl-, and silylacetylenes in neat water under copper-free conditions at 110 °C assisted by microwave irradiation. Using 0.5mol% of an oxime palladacycle as precatalyst, 2-dicyclohexylphosphino-2′,6′- dimethoxybiphenyl (SPhos, 2mol%) as ligand, hexadecyltrimethylammonium bromide (CTAB) as additive, and triethylamine (TEA) as base, a wide array of disubstituted alkynes has been prepared in good to high yields in only 30min. Copyright
Oxime-palladacycle-catalyzed suzuki-miyaura arylation and alkenylation of aryl imidazolesulfonates under aqueous and phosphane-free conditions
Civicos, Jose Francisco,Alonso, Diego A.,Najera, Carmen
supporting information; experimental part, p. 3670 - 3676 (2012/07/31)
Aryl and hetaroaryl imidazole-1-sulfonates are efficiently arylated and alkenylated with aryl- and alkenylboronic acids and potassium trifluoroborates by using 0.5 mol-% palladacycles 1 or Pd(OAc)2 at 110 °C under aqueous and phosphane-free conditions. Reactions can be performed by using conventional or microwave heating, leading to biaryls, stilbenes, and alkenylarenes in good to high yields, and high regio- and diastereoselectivities. The optimized methodology allows in situ phenol sulfonylation and one-pot Suzuki arylation or alkenylation as well as orthogonal functionalization of halogen-containing aryl imidazolesulfonates.
Phosphane-free suzukimiyaura coupling of aryl imidazolesulfonates with arylboronic acids and potassium aryltrifluoroborates under aqueous conditions#
Civicos, Jose Francisco,Gholinejad, Mohammad,Alonso, Diego A.,Najera, Carmen
supporting information; experimental part, p. 907 - 909 (2011/12/05)
Aryl imidazole-1-sulfonates are efficiently cross-coupled with arylboronic acids and potassium aryltrifluoroborates using only 0.5 mol% of oxime palladacycles 1 under aqueous conditions at 110 °C. Under these simple phosphane-free reaction conditions a wide array of biaryl derivatives has been prepared in high yields. This methodology allows in situ phenol sulfonation and one-pot Suzuki arylation as well as the employment of microwave irradiation conditions.
Anionic ortho-fries rearrangement, a facile route to arenol-based mannich bases
Assimomytis, Nikos,Sariyannis, Yiannis,Stavropoulos, Georgios,Tsoungas, Petros G.,Varvounis, George,Cordopatis, Paul
scheme or table, p. 2777 - 2782 (2010/03/03)
Phenol and 1-naphthol-based carbamates undergo the anionic ortho-Fries rearrangement to their corresponding amides. Bulky substitution at position 8 of 1-naphthol-based carbamates makes the rearrangement an exclusive reaction, even at -90 C, under a variety of conditions. The amides can be efficiently reduced to the corresponding Mannich bases. A novel route to 7-[(dialkylamino)methyl]-8- hydroxy-1-naphthaldehydes is presented.
