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1.
The N‐heterocyclic carbene (NHC)‐catalyzed oxidative amidation of aromatic aldehydes with amines in the presence of N‐bromosuccinimide (NBS) as an oxidant has been developed for the synthesis of amides. This amidation strategy is tolerant to both the electronic and the steric nature of the aryl aldehydes employed. The present methodology was extended to chiral amino acid derivatives to generate the corresponding amides in good yields and excellent ee values (>98%).
2.
Xiangcheng Pan Jacques Laleve Emmanuel Lacte Dennis P. Curran 《Advanced Synthesis \u0026amp; Catalysis》2013,355(18):3522-3526
Diphenyl disulfide (PhSSPh), a typical boryl monosulfide (diiPr‐Imd‐BH2SPh) and a typical boryl bis‐sulfide [diMe‐Imd‐BH(SPh)2] all serve as both initiators and precatalysts in the reduction of alkyl and aryl halides by readily available 1,3‐dimethylimidazol‐2‐ylidene⋅borane (diMe‐Imd‐BH3). The reactions are suggested to occur by a polarity reverse catalysis mechanism where in situ generated thiophenol is the active catalyst.
3.
Xue Song Shang Nian Tai Li Deng Yuan Li Pei Nian Liu 《Advanced Synthesis \u0026amp; Catalysis》2016,358(10):1577-1582
A convenient palladium‐catalyzed tandem reaction of aryl iodides and salicyl N‐tosylhydrazones has been achieved to afford a series of compounds containing the novel spiro[benzofuran‐3,2′‐chromene] scaffold in moderate to good yields. This efficient catalytic reaction, which tolerates various functional groups, combines alkyne‐based 5‐exo‐dig cyclization, palladium(II) carbene migratory insertion and intramolecular cyclization, generating three new bonds in one reaction.
4.
Herein a practical and efficient protocol for preparing a range of aminoisoquinolines is reported. Various aminoisoquinolines were prepared in moderate to good yields from the corresponding 2‐methylbenzonitriles and benzonitriles upon treatment with potassium tert‐butoxide.
5.
Qinquan Hu Yi Liu Xiaocong Deng Yanjun Li Yunfeng Chen 《Advanced Synthesis \u0026amp; Catalysis》2016,358(10):1689-1693
An aluminium(III) chloride‐catalyzed three‐component reaction of aromatic aldehydes, nitroalkanes, and sodium azide has been developed; this reaction sequence can be applied to a broad substrate scope and affords the corresponding 4‐aryl‐NH‐1,2,3‐triazoles in good to excellent yields. The milder reaction conditions and easier operation make this AlCl3‐catalyzed protocol more advantageous for the synthesis of 4‐aryl‐NH‐1,2,3‐triazoles.
6.
Takashi Otani Xue Jiang Kinryo Cho Rino Araki Noriki Kutsumura Takao Saito 《Advanced Synthesis \u0026amp; Catalysis》2015,357(7):1483-1492
Product selectivity control for the synthesis of imidoylindoles and 4‐alkylidenedihydroquinazolines from N‐imidoyl‐o‐alkynylanilines via silver triflate‐catalyzed cycloisomerization or tetrabutylammonium fluoride‐promoted cyclization is described. The product selectivity depends mainly on the catalyst/promoter used, and on the substituents on the alkyne and amidine functions of the substrates.
7.
Mourad Chioua Abdelouahid Samadi Elena Soriano Lourdes Infantes Jos Marco‐Contelles 《Advanced Synthesis \u0026amp; Catalysis》2014,356(6):1235-1241
We report here that the silver triflate‐catalyzed cyclization of 2‐amino‐6‐propargylamineazines affords new and highly functionalized iminoimidazoazines. We have investigated the scope and limitations of the present methodology, and some aspects of the reactivity of the resulting iminoimidazopyridines have been explored, and a DFT‐based mechanistic analysis of the silver triflate‐catalyzed cyclization has been undertaken.
8.
Beln Rubial Alfredo Ballesteros Jos M. Gonzlez 《Advanced Synthesis \u0026amp; Catalysis》2013,355(17):3337-3343
The first successful gold(I)‐catalyzed reaction of aryl aldehydes with trimethyl(arylethynyl)silanes to furnish bis‐alkynylated derivatives is reported. Key C C bond‐forming events involved in the catalytic cycle are analyzed.
9.
10.
Atsuhiro Iimuro Kosuke Higashida Yusuke Kita Kazushi Mashima 《Advanced Synthesis \u0026amp; Catalysis》2016,358(12):1929-1933
We describe a most straightforward synthetic method for preparing neurokinin‐1 (NK1) receptor antagonist derivatives by asymmetric hydrogenation of 3‐amido‐2‐arylpyridinium salts using dinuclear iridium complexes with enantiopure diphosphine ligands, affording the corresponding chiral piperidines in high cis‐diastereoselectivity (>95:5) and moderately high enantioselectivity (up to 86%). Deprotection treatments afforded the NK‐1 receptor antagonist (+)‐CP‐99,994 (83% ee). In addition, we observed unique additive effects of 10‐camphorsulfonic acid in the asymmetric hydrogenation of 3‐amido‐2‐arylpyridinium salts.
11.
Liu‐Yang Pu Ji‐Qiang Chen Mao‐Lin Li Yao Li Jian‐Hua Xie Qi‐Lin Zhou 《Advanced Synthesis \u0026amp; Catalysis》2016,358(8):1229-1240
A new strategy for the enantioselective construction of chiral 2,3‐cis‐dimethyldihydrobenzofurans has been developed by a ruthenium‐catalyzed asymmetric hydrogenation of racemic α‐aryloxybutanone via dynamic kinetic resolution (DKR), combined with a palladium‐catalyzed intramolecular reductive Heck cyclization. Starting from optically active 2,3‐cis‐dimethyldihydrobenzofuran, the natural products (+)/(−)‐PI‐220 and (+)‐3‐epi‐furaquinocin C were synthesized in high yields.
12.
A synthetically useful 1,3‐insertion reaction of a rhodium‐carbenoid into the C(sp2) H bond of simple indole is disclosed, which produces structurally divergent 2‐indolylenamides in good to excellent yields and decent chemo‐ and regioselectivities. The obtained tryptamine vinylogues can be transformed into biologically important tryptamine derivatives or 3,3′‐biindoles with ease.
13.
We have developed an electrophilic addition of allylic carbocations to 2‐cyclopropylidene‐2‐arylethanols constructing carbon‐carbon bonds with excellent regio‐ and stereoselectivities. The reaction affords 3‐oxabicyclo[3.2.0]heptanes in moderate to good yields via the electrophilic addition/ring‐opening/vinyl group shift/intramolecular cyclization sequence.
14.
Sandrine Ventre Etienne Derat Muriel Amatore Corinne Aubert Marc Petit 《Advanced Synthesis \u0026amp; Catalysis》2013,355(13):2584-2590
A simple hydrido‐cobalt complex efficiently catalyses the highly regio‐ and stereoselective dimerisation of various terminal arylacetylenes under mild conditions. The corresponding (E)‐1,4‐enynes are obtained as sole isomers with good to excellent yields. DFT calculations revealed that the reaction proceeds via a C H activation/hydrocobaltation pathway.
15.
Dennis U. Nielsen Signe Korsager Anders T. Lindhardt Troels Skrydstrup 《Advanced Synthesis \u0026amp; Catalysis》2014,356(17):3519-3524
An efficient three‐component reaction involving carbon monoxide with a range of aryl bromides and N‐substituted acetoacetamides is reported for the synthesis of β‐keto amides. This transformation is promoted by Pd‐catalysis followed by an acid‐mediated deacetylation upon work‐up, enabling a large number of β‐keto amides to be isolated. Finally, d2‐13C‐dyclonine could be synthesized in three steps utilizing the developed catalytic system as the key step.
16.
A more practical and efficient catalytic asymmetric chlorolactonization of styrene‐type carboxylic acids with 1,3‐dichloro‐5,5‐dimethylhydantoin (DCDMH) using C3‐symmetric cinchonine‐squaramide (CSCS) as organocatalyst has been developed. A series of chiral chloro‐substituted isochroman‐1‐ones was obtained in excellent yields (up to 95%) and enantioselectivities (up to 99% ee), whwereby the results for chloro‐substituted isochroman‐1‐ones are the best ever achieved. The catalyst can be recovered and reused for six cycles. Moreover, the chlorolactonization product 3b was further transformed to optically active bicyclic isochroman‐1‐one derivatives in high yield without losing the enantioselectivity. Furthermore, compounds 3e and 2n proved to be highly potent inhibitors of the HIV‐1 in TZM‐bl cells.
17.
Amandine Carrër Jean‐Daniel Brion Mouad Alami Samir Messaoudi 《Advanced Synthesis \u0026amp; Catalysis》2014,356(18):3821-3830
A straightforward assisted tandem palladium(II)‐ and palladium(0)‐catalyzed direct C‐3 and N‐4 arylation of quinoxalin‐2(1 H)‐ones with boronic acids and aryl halides in water as safe and cheap solvent is reported. This environmentally friendly catalytic protocol is compatible with a wide range of functional groups and allows construction of various biologically important quinoxalin‐2(1 H)‐one backbones.
18.
Yunyun Li Fen Wang Songjie Yu Xingwei Li 《Advanced Synthesis \u0026amp; Catalysis》2016,358(6):880-886
Iridium(III) and rhodium(III) complexes can catalyze the carbocyclization between 2‐phenylimidazo[1,2‐a]pyridine and α‐diazo esters. The reaction occurs via C H activation and dialkylation of the arene followed by intramolecular nucleophilic substitution. Iridium(III) and rhodium(III) catalysis offer complementary scopes with respect to the α‐diazo esters.
19.
Andrea Kii Michel Stephan Barbara Mohar 《Advanced Synthesis \u0026amp; Catalysis》2015,357(11):2540-2546
New 3rd generation designer ansa‐ruthenium(II) complexes featuring N,C‐alkylene‐tethered N,N‐dialkylsulfamoyl‐DPEN/η6‐arene ligands, exhibited good catalytic performance in the asymmetric transfer hydrogenation (ATH) of various classes of (het)aryl ketones in formic acid/triethylamine mixture. In particular, benzo‐fused cyclic ketones furnished 98 to >99.9% ee using a low catalyst loading.
20.
Dong‐Su Kim Jung‐Woo Park Chul‐Ho Jun 《Advanced Synthesis \u0026amp; Catalysis》2013,355(13):2667-2679
A new rhodium(III)‐catalyzed N‐annulation reaction of benzylamines with internal alkynes has been developed. Observations made during these efforts suggest that the mechanistic pathway followed in this process involves direct participation of benzylamines without their preliminary oxidative dehydrogenation. Moreover, N‐annulation reactions of primary benzylamines result in the formation of mixtures of isoquinolines and 8‐vinylisoquinolines. Finally, secondary and tertiary benzylamines undergo rhodium(III)‐catalyzed N‐annulation reactions to generate the respective isoquinolinium and hydroisoquinolinium salt products.