6335-52-0Relevant academic research and scientific papers
Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides
Colas, Kilian,Kohlhepp, Stefanie V.,Mendoza, Abraham,V. D. dos Santos, A. Catarina
supporting information, (2022/02/02)
The synthesis of ketones through addition of organometallic reagents to aliphatic carboxylic acids is a straightforward strategy that is limited to organolithium reagents. More desirable Grignard reagents can be activated and controlled with a bulky aniline-derived turbo-Hauser base. This operationally simple procedure allows the straightforward preparation of a variety of aliphatic and perfluoroalkyl ketones alike from functionalized alkyl, aryl and heteroaryl Grignard reagents.
Synthesis of Aliphatic Amides through a Photoredox Catalyzed Radical Carbonylation Involving Organosilicates as Alkyl Radical Precursors
Cartier, Alex,Levernier, Etienne,Dhimane, Anne-Lise,Fukuyama, Takahide,Ollivier, Cyril,Ryu, Ilhyong,Fensterbank, Louis
, p. 2254 - 2259 (2020/05/06)
Alkyl radicals, from primary to tertiary, formed by photocatalyzed oxidation of organosilicates, are involved efficiently in radical carbonylation with carbon monoxide (CO), in the presence of various amines and CCl4, leading to a variety of amides in moderate to good yields. (Figure presented.).
Nickel-catalyzed transamidation of aliphatic amide derivatives
Dander, Jacob E.,Baker, Emma L.,Garg, Neil K.
, p. 6433 - 6438 (2017/08/29)
Transamidation, or the conversion of one amide to another, is a long-standing challenge in organic synthesis. Although notable progress has been made in the transamidation of primary amides, the transamidation of secondary amides has remained underdeveloped, especially when considering aliphatic substrates. Herein, we report a two-step approach to achieve the transamidation of secondary aliphatic amides, which relies on non-precious metal catalysis. The method involves initial Boc-functionalization of secondary amide substrates to weaken the amide C-N bond. Subsequent treatment with a nickel catalyst, in the presence of an appropriate amine coupling partner, then delivers the net transamidated products. The transformation proceeds in synthetically useful yields across a range of substrates. A series of competition experiments delineate selectivity patterns that should influence future synthetic design. Moreover, the transamidation of Boc-activated secondary amide derivatives bearing epimerizable stereocenters underscores the mildness and synthetic utility of this methodology. This study provides the most general solution to the classic problem of secondary amide transamidation reported to date.
Copper-Catalyzed Carbonylative Synthesis of Aliphatic Amides from Alkanes and Primary Amines via C(sp3)-H Bond Activation
Li, Yahui,Zhu, Fengxiang,Wang, Zechao,Wu, Xiao-Feng
, p. 5561 - 5564 (2016/08/18)
Amides are important intermediates and building blocks in organic synthesis. Among the known preparation procedures, aminocarbonylation is an interesting and powerful tool. However, most of the studies were focused on noble metal-catalyzed synthesis of ar
Mild and Low-Pressure fac-Ir(ppy)3-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis
Chow, Shiao Y.,Stevens, Marc Y.,?kerbladh, Linda,Bergman, Sara,Odell, Luke R.
supporting information, p. 9155 - 9161 (2016/07/14)
A novel, mild and facile preparation of alkyl amides from unactivated alkyl iodides employing a fac-Ir(ppy)3-catalyzed radical aminocarbonylation protocol has been developed. Using a two-chambered system, alkyl iodides, fac-Ir(ppy)3, amines, reductants, and CO gas (released ex situ from Mo(CO)6), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a wide range of alkyl amides in moderate to excellent yields.
Low-Pressure Radical11C-Aminocarbonylation of Alkyl Iodides through Thermal Initiation
Chow, Shiao Y.,Odell, Luke R.,Eriksson, Jonas
, p. 5980 - 5989 (2016/12/26)
A radical11C-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into11C-labelled amides, including the 11β-HSD1 inhibitor [carbonyl-11C]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated11C-aminocarbonylation, which is limited to the preparation of11C-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon–[11C]CO delivery unit represents a simple and convenient alternative to previous radical11C-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.
Acid mediated deprotection of N-isopropyl tertiary amides
Lorenc, Chris,Reeves, Jonathan T.,Busacca, Carl A.,Senanayake, Chris H.
, p. 1280 - 1282 (2015/03/04)
Tertiary amides containing an N-isopropyl group were selectively deprotected by heating in methanesulfonic acid. The N-isopropyl group was removed selectively in the presence of other groups on the amide nitrogen such as methyl, primary alkyl, or aryl. The putative isopropyl cation was trapped by Friedel-Crafts alkylation of anisole when the latter was included as a co-solvent.
Photoinitiated carbonylation with [11C]carbon monoxide using amines and alkyl iodides
Itsenko, Oleksiy,Kihlberg, Tor,Langstroem, Bengt
, p. 4356 - 4360 (2007/10/03)
Photoinitiated radical carbonylation with [11C]carbon monoxide at low concentration was employed in syntheses of carbonyl-11C- labeled amides using alkyl iodides and amines as precursors. Eleven 11C-amides were synthesized
