5467-43-6Relevant academic research and scientific papers
Site-Selective Csp3-Csp/Csp3-Csp2Cross-Coupling Reactions Using Frustrated Lewis Pairs
Dasgupta, Ayan,Stefkova, Katarina,Babaahmadi, Rasool,Yates, Brian F.,Buurma, Niklaas J.,Ariafard, Alireza,Richards, Emma,Melen, Rebecca L.
supporting information, p. 4451 - 4464 (2021/04/07)
The donor-acceptor ability of frustrated Lewis pairs (FLPs) has led to widespread applications in organic synthesis. Single electron transfer from a donor Lewis base to an acceptor Lewis acid can generate a frustrated radical pair (FRP) depending on the s
Direct AlCl3-catalyzed transformation of benzyl THP ethers and allyl benzyl ethers
Bui, Tien Tan,Kim, Hee-Kwon
, p. 388 - 397 (2020/10/15)
THP and allyl groups are frequently used for the protection of alcohols. In this study, novel direct transformations of benzyl THP ethers and allyl benzyl ethers, protected forms of alcohols, are reported. TMSN3 and AlCl3 were employ
SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes
Martins, Guilherme M.,Back, Davi F.,Kaufman, Teodoro S.,Silveira, Claudio C.
, p. 3252 - 3264 (2018/03/25)
A novel and efficient SeCl2-mediated chalcogenative cyclization strategy toward 3-selenophen-3-yl-1H-indoles from readily available and conveniently substituted propargyl indoles is described. It entails an unprecedented selenirenium-induced 1,
Ligand-free Iron(II)-Catalyzed N-Alkylation of Hindered Secondary Arylamines with Non-activated Secondary and Primary Alcohols via a Carbocationic Pathway
Nayal, Onkar S.,Thakur, Maheshwar S.,Kumar, Manoranjan,Kumar, Neeraj,Maurya, Sushil K.
supporting information, p. 730 - 737 (2017/12/26)
Secondary benzylic alcohols represent a challenging class of substrates for N-alkylation of amines. Herein, we describe an iron(II)-catalyzed eco-friendly protocol for N-alkylation of secondary arylamines with secondary benzyl alcohols through a carbocationic pathway instead of the known borrowing hydrogen transfer (BHT) approach. Transiently generated carbocations, produced from alcohols via self-condensation, were coupled with arylamines to provide highly functionalized amine products. The scope of this methodology involves N-alkylation of primary, secondary and heterocyclic amines with primary/secondary benzylic, allylic and heterocyclic alcohols, which are common key structures in numerous pharmaceuticals drugs. The method can also be easily adopted for the amination of various natural products. (Figure presented.).
Cleavage of C–C and C–O Bonds to Form C–C Bonds: Direct Cross-Coupling between Acetylenic Alcohols and Benzylic Carbonates
Mi, Zhiyuan,Tang, Jiahao,Guan, Zhipeng,Shi, Wei,Chen, Hao
, p. 4479 - 4482 (2018/09/10)
A palladium-catalyzed cross-coupling reaction between C(sp) and C(sp3) centers was achieved in excellent yields via C–C bond cleavage and C–O bond cleavage. This procedure uses relatively stable acetylenic alcohols as reactants instead of unsta
An Atom-Economical Route to Substituted β-Arylethyl Ketones: Phosphomolybdic Acid-Catalyzed Carbohydroxylation of Terminal Alkynes in Organic Carbonate
Yang, Guo-Ping,Zhang, Nan,Ma, Nuan-Nuan,Yu, Bing,Hu, Chang-Wen
supporting information, p. 926 - 932 (2017/03/27)
A highly efficient and atom-economical route for the synthesis of substituted β-arylethyl ketones was developed by using cheap phosphomolybdic acid (H3PMo12O40) as catalyst and non-volatile propylene carbonate (PC) as green solvent via the carbohydroxylation of terminal alkynes with benzylic alcohols under mild conditions. Various functional groups on the benzylic alcohols and terminal alkynes were tolerated, giving the corresponding substituted β-arylethyl ketones as products in good to excellent yields (up to 95%). It is worth noting that a turnover number (TON) of up to 520 was achieved in the protocol. The mechanism investigation showed that PC might stabilize the heteropoly anion and the carbocation intermediate thus facilitating the carbohydroxylation reaction. (Figure presented.).
Photosensitizer-Free Visible-Light-Mediated Gold-Catalyzed 1,2-Difunctionalization of Alkynes
Huang, Long,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 4808 - 4813 (2016/04/19)
Under visible-light irradiation, the gold-catalyzed intermolecular difunctionalization of alkynes with aryl diazonium salts in methanol affords a variety of α-aryl ketones in moderate to good yields. In contrast to previous reports on gold-catalyzed reactions that involve redox cycles, no external oxidants or photosensitizers are required. The reaction proceeds smoothly under mild reaction conditions and shows broad functional-group tolerance. Further applications of this method demonstrate the general applicability of the arylation of a vinyl gold intermediate instead of the commonly used protodemetalation step. This step provides facile access to functionalized products in one-pot processes. With a P,N-bidentate ligand, a stable aryl gold(III) species was obtained, which constitutes the first direct experimental evidence for the commonly postulated direct oxidative addition of an aryl diazonium salt to a pyridine phosphine gold(I) complex.
Synthesis of tertiary arylamines: Lewis acid-catalyzed direct reductive: N -alkylation of secondary amines with ketones through an alternative pathway
Nayal, Onkar S.,Thakur, Maheshwar S.,Bhatt, Vinod,Kumar, Manoranjan,Kumar, Neeraj,Singh, Bikram,Sharma, Upendra
, p. 9648 - 9651 (2016/08/04)
We report herein a highly efficient, tin(ii)/PMHS catalyzed reductive N-alkylation of arylamines with ketones affording tertiary arylamines. A very wide substrate scope was observed for the current catalytic method as all six permutations of ketones/aldehydes/heterocyclic carbonyls and primary/secondary/heterocyclic amines were well tolerated, enabling access to secondary, tertiary and heterocyclic amines. The method is also convenient for the synthesis of N-substituted isoindolinones and phthalazinones via a tandem amination-amidation sequence. Mechanistic investigations revealed a carbocationic pathway instead of an ordinary direct reductive amination pathway.
Br?nsted Acid-Catalyzed Reactions of Trifluoroborate Salts with Benzhydryl Alcohols
Fisher, Kayla M.,Bolshan, Yuri
, p. 12676 - 12685 (2016/01/09)
Br?nsted acid-catalyzed carbon-carbon bond forming methodology using potassium alkynyl- and alkenyltrifluoroborate salts has been developed. Organotrifluoroborates react with benzhydryl alcohols to afford a broad range of alkynes and alkenes in good to excellent yields. This protocol features good atom economy because organotrifluoroborate salts and alcohols react in a 1:1 ratio. Furthermore, a variety of unprotected functional groups were tolerated under the developed conditions, including amide, aldehyde, free hydroxyl, and carboxylic acid.
Direct Dehydroxylative Coupling Reaction of Alcohols with Organosilanes through Si-X Bond Activation by Halogen Bonding
Saito, Masato,Tsuji, Nobuya,Kobayashi, Yusuke,Takemoto, Yoshiji
supporting information, p. 3000 - 3003 (2015/06/30)
The combined use of a halogen bond (XB) donor with trimethylsilyl halide was found to be an efficient cocatalytic system for the direct dehydroxylative coupling reaction of alcohol with various nucleophiles, such as allyltrimethylsilane and trimethylcyanide, to give the corresponding adduct in moderate to excellent yields. Detailed control experiments and mechanistic studies revealed that the XB interaction was crucial for the reaction. The application of this coupling reaction is also described.
