Hiroaki Murayama, Kazunori Nagao, Hirohisa Ohmiya, and Masaya Sawamura
Org. Lett., 2016, 18 (7), pp 1706–1709
Publication Date (Web): March 24, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00677
Phosphine organocatalysis enabled vicinal acylcyanation of alkynoates with acyl cyanides to form acrylonitrile derivatives with a tetrasubstituted alkene moiety. The acyl and cyano groups were introduced at the α and β carbon atoms, respectively, of the C–...
Shino Ubukata, Jun-ichi Ito, Ryota Oguri, and Hisao Nishiyama
J. Org. Chem., 2016, 81 (8), pp 3347–3355
Publication Date (Web): March 23, 2016 (Article)
DOI: 10.1021/acs.joc.6b00374
Catalytic asymmetric three-component coupling reactions of terminal alkynes, α,β-unsaturated ketones, and aldehydes were studied. The chiral ruthenium complexes containing bis(oxazolinyl)phenyl ligands were found to serve as efficient catalysts for a ...
Yuta Hamachi, Moe Katano, Yohei Ogiwara, and Norio Sakai
Org. Lett., 2016, 18 (7), pp 1634–1637
Publication Date (Web): March 22, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00508
A novel synthesis of α-aminonitriles is described via an indium-catalyzed three-component coupling reaction of alkynes, amines, and trimethylsilyl cyanide (Me3SiCN). Hydroamination of alkynes with a subsequent nucleophilic addition of Me3SiCN resulted in ...
Yuran Wang, Jennifer D. Lewis, and Yuriy Román-Leshkov
ACS Catal., Articles ASAP (As Soon As Publishable), pp 2739–2744
Publication Date (Web): March 21, 2016 (Letter)
DOI: 10.1021/acscatal.6b00561
Lewis acidic zeolites are used to synthesize unsaturated dicarboxylic acid esters via aldol condensation of keto esters. Hafnium-containing BEA (Hf-BEA) zeolites catalyze the condensation of ethyl pyruvate into diethyl 2-methyl-4-oxopent-2-enedioate and ...
Stig D. Friis, Anders T. Lindhardt, and Troels Skrydstrup
Acc. Chem. Res., Articles ASAP (As Soon As Publishable)
Publication Date (Web): March 21, 2016 (Article)
DOI: 10.1021/acs.accounts.5b00471
Conspectus
Low molecular weight gases (e.g., carbon monoxide, hydrogen, and ethylene) represent vital building blocks for the construction of a wide array of organic molecules. Whereas experimental organic chemists routinely handle solid and liquid ...
Org. Lett., 2016, 18 (7), pp 1510–1513
Publication Date (Web): March 17, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00028
A nickel-catalyzed three-component hydrocarboxylation of diynes with ZnEt2 and CO2 (1 atm) is disclosed. With this method, symmetric/nonsymmetric diynes could be reacted smoothly with very high stereo- and regioselectivity, affording conjugated 2,4-...
Michiko Sasaki, Masafumi Ando, Masatoshi Kawahata, Kentaro Yamaguchi, and Kei Takeda
Org. Lett., 2016, 18 (7), pp 1598–1601
Publication Date (Web): March 17, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00455
Siloxy-N-silylketenimines generated in situ from O-silyl cyanohydrins were converted to α-ketoamides by brief exposure to air or oxygen. Oxidation under extremely mild conditions can be explained by assuming the intermediacy of a 3-imino-1,2-dioxetane ...
Martina Spallarossa, Qian Wang, Renata Riva, and Jieping Zhu
Org. Lett., 2016, 18 (7), pp 1622–1625
Publication Date (Web): March 16, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00483
The reaction of isocyanomethylenetriphenylphosphorane, generated in situ from the corresponding phosphonium salt, with a diverse set of aldehydes afforded vinyl isocyanides in good to high yields. Excellent E-selectivity was observed for aliphatic ...
Tian-Yang Yu, Hao Wei, Yong-Chun Luo, Yao Wang, Zhu-Yin Wang, and Peng-Fei Xu
J. Org. Chem., 2016, 81 (7), pp 2730–2736
Publication Date (Web): March 15, 2016 (Article)
DOI: 10.1021/acs.joc.5b02618
An efficient one-pot method for the syntheses of di- and polybrominated esters from readily available aldehydes is reported. The direct use of the in situ generated byproduct PPh3O in the following reactions greatly improves the efficiency of the cascade. ...
Zongjun Qiao and Xuefeng Jiang
Org. Lett., 2016, 18 (7), pp 1550–1553
Publication Date (Web): March 14, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00324
A divergent cross-coupling for both thioether and thioester construction from organosilicon compounds has been developed. Predominant selectivity for Hiyama-type coupling and C1 insertion reaction was achieved under the guidance of ligands. Thioether was ...
Xuefeng Tan, Guozhen Wang, Ziyue Zhu, Conghui Ren, Jinping Zhou, Hui Lv, Xiaoyong Zhang, Lung Wa Chung, Lina Zhang, and Xumu Zhang
Org. Lett., 2016, 18 (7), pp 1518–1521
Publication Date (Web): March 14, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00060
A readily available ruthenium(II) catalyst was developed for the catalytic hydrogenation of aldehydes with a TON (turnover number) up to 340000. It can be performed without base and solvent, showing highly industrial potential. High chemoselectivity can ...
Yang Li, Ping Deng, Youmao Zeng, Yan Xiong, and Hui Zhou
Org. Lett., 2016, 18 (7), pp 1578–1581
Publication Date (Web): March 14, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00432
A novel heterobimetallic Cu/Sm/aminophenol sulfonamide complex has been developed by a convenient one-pot method for the anti-selective asymmetric Henry reaction. The corresponding anti-β-nitro alcohols are obtained in up to 99% yield, >30:1 dr, and 98% ...
Nikolaus Gorgas, Berthold Stöger, Luis F. Veiros, and Karl Kirchner
ACS Catal., 2016, 6 (4), pp 2664–2672
Publication Date (Web): March 11, 2016 (Research Article)
DOI: 10.1021/acscatal.6b00436
The synthesis and application of [Fe(PNPMe-iPr)(CO)(H)(Br)] and [Fe(PNPMe-iPr)(H)2(CO)] as catalysts for the homogeneous hydrogenation of aldehydes is described. These systems were found to be among the most efficient catalysts for this process reported ...
Yoshiya Fukumoto, Yuto Tamura, Yasuaki Iyori, and Naoto Chatani
J. Org. Chem., 2016, 81 (8), pp 3161–3167
Publication Date (Web): March 11, 2016 (Article)
DOI: 10.1021/acs.joc.6b00116
The combination of TpRh(C2H4)2 (Tp = tris(pyrazol-1-yl)borate) and P(2-furyl)3 catalyzes the reaction of tertiary alkyl-substituted alkynes with tert-butylhydrazine, leading to the formation of 3,3,3-trisubstituted propionitrile derivatives. This reaction ...
Ming-Chen Fu, Rui Shang, Wan-Min Cheng, and Yao Fu
ACS Catal., 2016, 6 (4), pp 2501–2505
Publication Date (Web): March 10, 2016 (Letter)
DOI: 10.1021/acscatal.6b00276
By the combination of a Ni(II) salt, a bisphosphine ligand, and a catalytic amount of carboxylic acid anhydride, atom-economic hydrocarboxylation of various alkynes with formic acid can be achieved with high selectivity and remarkable functional group ...
Rémi Blieck, Janet Bahri, Marc Taillefer, and Florian Monnier
Org. Lett., 2016, 18 (6), pp 1482–1485
Publication Date (Web): March 9, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00452
The ligand-free copper-catalyzed hydroamination of allenes has been accomplished in the presence of cyclic secondary amines or anilines derivatives. This novel methodology undergoes the selective generation of (E)-allylamines under smooth conditions with ...
Victoria J. Garza and Michael J. Krische
J. Am. Chem. Soc., 2016, 138 (11), pp 3655–3658
Publication Date (Web): March 9, 2016 (Communication)
DOI: 10.1021/jacs.6b01078
Chiral iridium complexes modified by SEGPHOS catalyze the 2-propanol-mediated reductive coupling of branched allylic acetates 1a–1o with formaldehyde to form primary homoallylic alcohols 2a–2o with excellent control of regio- and enantioselectivity. These ...
Clément Lebée, Morgan Languet, Clémence Allain, and Géraldine Masson
Org. Lett., 2016, 18 (6), pp 1478–1481
Publication Date (Web): March 7, 2016 (Letter)
DOI: 10.1021/acs.orglett.6b00442
A general and practical photoredox-promoted addition of nucleophiles to N-acylimines generated in situ from α-amidosulfides using Ru(bpy)3(PF6)2 as the photocatalyst is reported. The broad scope of the reaction toward various nucleophiles and amidosulfide ...
Xin Li, Xing Che, Gui-Hua Chen, Jun Zhang, Jia-Lei Yan, Yun-Fei Zhang, Li-Sheng Zhang, Chao-Ping Hsu, Yi Qin Gao, and Zhang-Jie Shi
Org. Lett., 2016, 18 (6), pp 1234–1237
Publication Date (Web): March 7, 2016 (Letter)
DOI: 10.1021/acs.orglett.5b03690
By employing a simple, inexpensive, and transition-metal-free oxidation system, secondary C–H bonds in a series of phthaloyl protected primary amines and amino acid derivatives were oxidized to carbonyls with good regioselectivities. This method could ...
ACS Catal., 2016, 6 (4), pp 2515–2524
Publication Date (Web): March 7, 2016 (Perspective)
DOI: 10.1021/acscatal.6b00048
The latest advances in the field of gold-catalyzed divergent synthesis of carbo- and heterocycles are highlighted in this Perspective. These gold-catalyzed reactions, which can provide structurally novel carbo- and heterocycles, were achieved with good ...
