CC Bond Formation

Name Reactions

Recent Literature

A highly convenient way to perform the synthesis of alkynes from aldehydes utilizes a new in situ preparation of dimethyldiazomethylphosphonate. As a consequence a commercially available reagent can now be used, circumventing a disadvantage of earlier protocols.
T. Gers, D. Kunce, P. Markowski, J. Izdebski, Synthesis, 2003, 37-42.

(Z)-1-Bromo-1-alkenes were stereoselectively efficiently prepared in high yields by microwave irradiation of the corresponding anti-2,3-dibromoalkanoic acids in DMF using Et₃N as base. Microwave-assisted one-pot syntheses of terminal alkynes and enynes from 2,3-dibromoalkanoic acids were also developed.
C. Kuang, Q. Yang, H. Senboku, M. Tokuda, Tetrahedron, 2005, 61, 4043-4052.

The ionic liquid 1-methyl-3-pentylimidazolium fluoroborate, [pmIm]BF₄, is an efficient catalyst as well as solvent for the stereoselective debromination of various vicinal-dibromides to the corresponding (E)-alkenes in high yields under microwave irradiation. This reaction does not require any conventional reducing agent, and the ionic liquid can be recycled.
B. C. Ranu, R. Jana, J. Org. Chem., 2005, 70, 8621-8624.

Dichloroindium hydride (Cl₂InH) generated in situ from the combination of a catalytic amount of indium(III) chloride and sodium borohydride in acetonitrile reduces activated vic-dibromides to the corresponding (E)-alkenes in excellent yields.
B. C. Ranu, A. Das, A. Hajira, Synthesis, 2003, 1012-1014.

An efficient, palladium-catalyzed synthesis of 2-alkene-4-ynoates and -nitriles by a simple reaction of vic-diiodo-(E)-alkenes with acrylic esters and nitriles in water leads to (E)-isomers from acrylic esters exclusively, whereas (Z)-isomers are obtained in high stereoselectivity from reactions of acrylonitrile. The in situ prepared Pd(0) nanoparticles can be recycled.
B. C. Ranu, K. Chattopadhyay, Org. Lett., 2007, 9, 2409-2412.

B. C. Ranu, K. Chattopadhyay, Org. Lett., 2007, 9, 2409-2412.

Deprotonation of 3,3,3-trichloropropyl-1-triphenylphosphonium chloride generates the corresponding phosphorane, which reacts with aldehydes to give trichloromethylated (Z)-olefins, which are useful for the synthesis of (Z)-1,3-enynes, (Z,Z)-1-chloro-1,3-dienes, and 1,3-diynes in high yields and stereospecificities.
M. S. Karatholuvhu, P. L. Fuchs, J. Am. Chem. Soc., 2004, 126, 14314-14315.