Regio- and stereo-selective decarbonylative alkylative arylation of terminal alkynes with aliphatic aldehydes and arenes via dual C–H bond functionalization

2019 ◽  
Vol 6 (20) ◽  
pp. 3597-3602
Author(s):  
Yong Peng ◽  
Feng Zhang ◽  
Ting-Ting Qin ◽  
Cong-Ling Xu ◽  
Luo Yang
Keyword(s):  
Terminal Alkynes ◽  
Aliphatic Aldehydes ◽  
Bond Functionalization ◽  
Alkyl Radicals ◽  
Sugar Derivatives

Readily available linear/branched aliphatic aldehydes including sugar derivatives were oxidatively decarbonylated into 1˙, 2˙ and 3˙ alkyl radicals for the alkylative arylation of terminal alkynes via dual C–H bond functionalization.

Co-Catalyzed decarbonylative alkylative esterification of styrenes with aliphatic aldehydes and hypervalent iodine(iii) reagents

2019 ◽  
Vol 6 (17) ◽  
pp. 3065-3070 ◽  
Author(s):  
Yong Peng ◽  
Yuan-Yuan Jiang ◽  
Xue-Jiao Du ◽  
Da-You Ma ◽  
Luo Yang
Keyword(s):  
Radical Addition ◽  
Hypervalent Iodine ◽  
Aliphatic Aldehydes ◽  
Alkyl Radicals

Decarbonylation of aliphatic aldehydes into 1°, 2° and 3° alkyl radicals to construct C(sp3)–C(sp3) bond via radical addition and C(sp3)–O bond via the interconversion of CoII–CoIII–CoI.

scholarly journals Synthesis of Pyridines from Ketoximes and Terminal Alkynes via C–H Bond Functionalization

2012 ◽  
Vol 77 (5) ◽  
pp. 2501-2507 ◽  
Author(s):  
Rhia M. Martin ◽  
Robert G. Bergman ◽  
Jonathan A. Ellman
Keyword(s):  
Terminal Alkynes ◽  
Bond Functionalization

Metal-free cascade oxidative decarbonylative alkylarylation of acrylamides with aliphatic aldehydes: a convenient approach to oxindoles via dual C(sp2)–H bond functionalization

2016 ◽  
Vol 18 (10) ◽  
pp. 2941-2945 ◽  
Author(s):  
Luo Yang ◽  
Wen Lu ◽  
Wang Zhou ◽  
Feng Zhang
Keyword(s):  
Aliphatic Aldehydes ◽  
Bond Functionalization ◽  
Metal Free ◽  
Convenient Approach

A convenient metal-free cascade oxidative decarbonylative alkylarylation of acrylamides with aliphatic aldehydes to provide quaternary oxindoles is developed.

Orthoamides and Iminium Salts, LXXX [1]. C-Glycosyl Alkynecarboxylic Acid Orthoamides. Versatile Intermediates in the Synthesis of New Types of Highly Substituted C-Nucleoside Analogs

2012 ◽  
Vol 67 (7) ◽  
pp. 699-716 ◽  
Author(s):  
Konstantin Drandarov ◽  
Willi Kantlehner
Keyword(s):  
Model Compound ◽  
Nucleoside Analogs ◽  
Building Blocks ◽  
2D Nmr ◽  
General Character ◽  
Terminal Alkynes ◽  
Iminium Salts ◽  
Synthetic Strategy ◽  
Nmr Techniques ◽  
Sugar Derivatives

The C-glycosyl alkynecarboxylic acid orthoamides 22 and 23 are proposed as versatile precursors for the synthesis of new types of C-nucleoside analogs. The new synthetic strategy includes alkynylation of protected aldoses 13 or ketoses by Grignard ethynylation or Barbier propargylation, O-protection of the resulting alkynols 14-16, and nucleophilic addition of the metalated protected terminal alkynes 20 and 21 to peralkylguanidinium salt 2 to afford the corresponding alkynecarboxylic acid orthoamides 22 and 23, which in reactions with mono or bis-nucleophiles could serve as building blocks for the construction of a wide variety of C-nucleoside-like binary conjugates. All the steps are demonstrated on 2,4,3,5-bis(4-methoxybenzylidene)-protected L-xylose 11 as a model compound. The synthesis of a representative series of C-glycosidic conjugates of highly substituted “push-pull” 1,3-butadienes 32-35, pyrimidines 24-31, and 2-pyridones 36-39 is included. The stereochemistry of all described compounds is established by 2D-NMR techniques. A general character of the proposed synthetic strategy, when applied to different appropriately protected sugar derivatives, is suggested, and a biomedical applicability of the described type of conjugates is expected.

ChemInform Abstract: Synthesis of Pyridines from Ketoximes and Terminal Alkynes via C-H Bond Functionalization.

ChemInform ◽  
2012 ◽  
Vol 43 (27) ◽  
pp. no-no
Author(s):  
Rhia M. Martin ◽  
Robert G. Bergman ◽  
Jonathan A. Ellman
Keyword(s):  
Terminal Alkynes ◽  
Bond Functionalization

Fe-Promoted Chlorobenzylation of Terminal Alkynes through Benzylic C(sp3)–H Bond Functionalization

2016 ◽  
Vol 18 (6) ◽  
pp. 1238-1241 ◽  
Author(s):  
Jiang-Ling Shi ◽  
Ji-Cheng Zhang ◽  
Bi-Qin Wang ◽  
Ping Hu ◽  
Ke-Qing Zhao ◽  
...  
Keyword(s):  
Terminal Alkynes ◽  
Bond Functionalization

Silver-catalyzed direct selenylation of terminal alkynes through C H bond functionalization

2017 ◽  
Vol 427 ◽  
pp. 73-79 ◽  
Author(s):  
Maurício C.D.F. Xavier ◽  
Bruna Goldani ◽  
Ricardo F. Schumacher ◽  
Gelson Perin ◽  
Paulo Henrique Schneider ◽  
...  
Keyword(s):  
Terminal Alkynes ◽  
Bond Functionalization
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