Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols

被引:77
作者
Biswas, Nandita [1 ]
Sharma, Rahul [1 ]
Srimani, Dipankar [1 ]
机构
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, Assam, India
关键词
Ruthenium; homogeneous catalysis; tridentate ligands; alkylation; borrowing hydrogen; indole; ONE-POT SYNTHESIS; BORROWING HYDROGEN; TRYPTAMINE DERIVATIVES; SUSTAINABLE SYNTHESIS; REDOX CONDENSATION; O-NITROANILINES; AMINO-ALCOHOLS; METHANOL; DEHYDROGENATION; TRANSITION;
D O I
10.1002/adsc.202000326
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via "borrowing hydrogen" strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives.
引用
收藏
页码:2902 / 2910
页数:9
相关论文
共 95 条
[1]   First-Row Transition Metal (De)Hydrogenation Catalysis Based On Functional Pincer Ligands [J].
Alig, Lukas ;
Fritz, Maximilian ;
Schneider, Sven .
CHEMICAL REVIEWS, 2019, 119 (04) :2681-2751
[2]  
[Anonymous], 2018, ANGEW CHEM-GER EDIT
[3]   Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].
Austin, JF ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173
[4]   Iron(II) Chloride-1,1′-Binaphthyl-2,2′-diamine (FeCl2-BINAM) Complex Catalyzed Domino Synthesis of Bisindolylmethanes from Indoles and Primary Alcohols [J].
Badigenchala, Sindhura ;
Ganapathy, Dhandapani ;
Das, Ankita ;
Singh, Rahul ;
Sekar, Govindasamy .
SYNTHESIS-STUTTGART, 2014, 46 (01) :101-109
[5]  
Barden T. C., 2010, HETEROCYCLIC SCAFFOL, V26, P31
[6]   Catalytic Conversion of Nonfood Woody Biomass Solids to Organic Liquids [J].
Barta, Katalin ;
Ford, Peter C. .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1503-1512
[7]   Observations concerning the synthesis of tryptamine homologues and branched tryptamine derivatives via the borrowing hydrogen process: synthesis of psilocin, bufotenin, and serotonin [J].
Bartolucci, Silvia ;
Mari, Michele ;
Di Gregorio, Giovanni ;
Piersanti, Giovanni .
TETRAHEDRON, 2016, 72 (18) :2233-2238
[8]   Iridium-Catalyzed Direct Synthesis of Tryptamine Derivatives from Indoles: Exploiting N-Protected β-Amino Alcohols as Alkylating Agents [J].
Bartolucci, Silvia ;
Mari, Michele ;
Bedini, Annalida ;
Piersanti, Giovanni ;
Spadoni, Gilberto .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (06) :3217-3222
[9]   VIBRINDOLE-A, A METABOLITE OF THE MARINE BACTERIUM, VIBRIO-PARAHAEMOLYTICUS, ISOLATED FROM THE TOXIC MUCUS OF THE BOXFISH OSTRACION-CUBICUS [J].
BELL, R ;
CARMELI, S ;
SAR, N .
JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1994, 57 (11) :1587-1590
[10]  
Berendt B. G. R., 2020, EUR J ORG CHEM, P1136