Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams

• Valentina Giraldi,
• Giandomenico Magagnano,
• Daria Giacomini,
• Pier Giorgio Cozzi and
• Andrea Gualandi

Beilstein J. Org. Chem. 2024, 20, 2461–2468, doi:10.3762/bjoc.20.210

• , Via Gobetti 85, 40129 Bologna, Italy 10.3762/bjoc.20.210 Abstract The direct nucleophilic addition of amides to unfunctionalized alkenes via photoredox catalysis represents a facile approach towards functionalized alkylamides. Unfortunately, the scarce nucleophilicity of amides and competitive side

Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols

• Smaher E. Butt,
• Konrad Kepski,
• Jean-Marc Sotiropoulos and
• Wesley J. Moran

Beilstein J. Org. Chem. 2024, 20, 2455–2460, doi:10.3762/bjoc.20.209

• cyclization of para-substituted benzamides and chloro- (7b), bromo- (7c), phenyl- (7d), and methoxy- (7e) derivatives were all isolated in moderate yields. The ortho-substituted derivatives 7f, 7g, and 7h were also successfully prepared. Alkylamides were found to be ambiguous substrates as the acetamide 7i

1-Imidoalkylphosphonium salts with modulated C_α–P⁺ bond strength: synthesis and application as new active α-imidoalkylating agents

• Jakub Adamek,
• Roman Mazurkiewicz,
• Anna Węgrzyk and
• Karol Erfurt

Beilstein J. Org. Chem. 2017, 13, 1446–1455, doi:10.3762/bjoc.13.142

• products [3][4][5][6][7][8][9][10][11][12]. Most of the α-amidoalkylating reagents possess the structure of α-functionalized N-alkylamides 1, where Z = OH, OR, OCOR, Cl, Br, I, NHCOR, SO2Ar, 1-benzotriazolyl or PPh3+ X− and acts as a nucleofugal leaving group (Scheme 1) [3][8][9][10][13][14][15][16][17][18

Synthesis of β-arylated alkylamides via Pd-catalyzed one-pot installation of a directing group and C(sp³)–H arylation

• Yunyun Liu,
• Yi Zhang,
• Xiaoji Cao and
• Jie-Ping Wan

Beilstein J. Org. Chem. 2016, 12, 1122–1126, doi:10.3762/bjoc.12.108

• .12.108 Abstract The synthesis of β-arylated alkylamides via alkyl C–H bond arylation has been realized by means of direct one-pot reactions of acyl chlorides, aryl iodides and 8-aminoquinoline. Depending on the structure of the starting materials, both single and double β-arylated alkylamides could be

• accessed. Keywords: alkylamides; C–H arylation; directing group; in situ installation; one-pot; Introduction The elaboration of inert C–H bonds is regarded as the longstanding aim of modern organic synthesis. Upon the extensive efforts during the past decades, the exploration and application of C–H

• functionalization chemistry [35][36][37][38][39][40], we have executed efforts to the AQ-assisted β-C–H functionalization reactions of alkylamides via activation of the C(sp3)–H bond, a classical protocol toward β-arylamide synthesis. While the known examples, including C(sp3)–H alkylation, arylation or oxygenation

Recent advances in copper-catalyzed C–H bond amidation

• Jie-Ping Wan and
• Yanfeng Jing

Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240

• sulfonamidation and imidation) reactions under the categories of C(sp3)–H bond amidation, C(sp2)–H bond amidation, C(sp)–H bond amidation and cascade reactions initiated by C–H amidation. Review C(sp3)–H bond amidation Intermolecular amidation The formation of N-alkylamides could be traditionally accessed via

• nucleophilic N-alkylation of amides by using pre-functionalized electrophiles such as alkyl halides, alcohols or amines [36][37][38][39][40][41]. An alternative tactic which employs raw C–H bond conversion represents a revolutionary step in the synthesis of N-alkylamides. In 2007, Fu and co-workers [42

• adjacent to oxygen via an N-halosuccinimide- (NCS or NBS)-assisted copper-catalyzed process. As shown in Scheme 2, both cyclic and acyclic compounds 6 containing a benzylic C–H bond could be readily converted to N-alkylamides 8 or sulfonamides 9 via this much milder catalytic method. In addition, this