1993 R.U. Lemieux Award Lecture Organometallic-type reactions in aqueous media—a new challenge in organic synthesis

1994 ◽  
Vol 72 (5) ◽  
pp. 1181-1192 ◽  
Author(s):  
T.H. Chan ◽  
C.J. Li ◽  
M.C. Lee ◽  
Z.Y. Wei
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Organic Solvents ◽  
Carbonyl Compounds ◽  
Aqueous Media ◽  
Coupling Reactions ◽  
Homoallylic Alcohols ◽  
Allyl Halides ◽  
Nonulosonic Acid

The development of organometallic-type reactions in aqueous media is reviewed. Coupling reactions of allyl halides with carbonyl compounds mediated by zinc, or tin, or indium in aqueous media to give homoallylic alcohols are discussed. The stereochemical outcome is compared with similar reactions in organic solvents. A concise synthesis of (+)-muscarine is used to illustrate the usefulness of aqueous organometallic-type reactions in organic synthesis. The procedure to protect–deprotect hydroxy functional groups may not be necessary in these reactions. An application in the carbohydrate area is demonstrated with the synthesis of (+)-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). The mechanistic possibilities of organometallic-type reactions in aqueous media are outlined.

Transition-Metal-Free Synthetic Strategies for the Cross-Coupling Reactions in Water: A Green Approach

2020 ◽  
Vol 07 ◽  
Author(s):  
Tanmay Chatterjee ◽  
Nilanjana Mukherjee
Keyword(s):  
Transition Metal ◽  
Organic Solvents ◽  
Aqueous Media ◽  
Cross Coupling ◽  
Transition Metal Catalysts ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Green Approach ◽  
Dehydrogenative Coupling

Abstract: A natural driving force is always working behind the synthetic organic chemists towards the development of ‘green’ synthetic methodologies for the synthesis of useful classes of organic molecules having potential applications. The majority of the essential classes of organic transformations, including C-C and C-X (X = heteroatom) bond-forming crosscoupling reactions, cross dehydrogenative-coupling (CDC) mostly rely on the requirement of transition-metal catalysts and hazardous organic solvents. Hence, the scope in developing green synthetic strategies by avoiding the use of transitionmetal catalysts and hazardous organic solvents for those important and useful classes of organic transformations is very high. Hence, several attempts are made so far. Water being the most abundant, cheap, and green solvent in the world; numerous synthetic methods have been developed in an aqueous medium. In this review, the development of transitionmetal- free green synthetic strategies for various important classes of organic transformations such as C-C and C-X bondforming cross-coupling, cross dehydrogenative-coupling, and oxidative-coupling in an aqueous media is discussed.

Organometallic reactions in aqueous media — Antimony-mediated allylation of carbonyl compounds and the nature of allylstibine intermediates

2001 ◽  
Vol 79 (11) ◽  
pp. 1536-1540
Author(s):  
Lian-Hai Li ◽  
Tak Hang Chan
Keyword(s):  
Carbonyl Compounds ◽  
Good Yield ◽  
Allyl Bromide ◽  
Aqueous Media ◽  
Organometallic Reactions ◽  
Homoallylic Alcohols ◽  
Reaction Proceeds

Commercial antimony metal, in aqueous 1 M H(D)Cl solution, reacts with allyl bromide and aldehydes to give the corresponding homoallylic alcohols in good yield. The reaction proceeds through the formation of allylstibine intermediates. The structures of the allylstibine intermediates are likely to be allylstibine dibromide and diallylstibine bromide.Key words: allylation reaction, aqueous organometallic reactions, homoallylic alcohols, allylstibine dibromide, diallylstibine bromide.

scholarly journals Comparative Studies on Conventional and Ultrasound-Assisted Synthesis of Novel Homoallylic Alcohol Derivatives Linked to Sulfonyl Dibenzene Moiety in Aqueous Media

2013 ◽  
Vol 2013 ◽  
pp. 1-9 ◽  
Author(s):  
Mohamed F. Mady ◽  
Ahmed A. El-Kateb ◽  
Ibrahim F. Zeid ◽  
Kåre B. Jørgensen
Keyword(s):  
Spectral Data ◽  
Comparative Studies ◽  
Carbonyl Compounds ◽  
Aqueous Media ◽  
Reaction Times ◽  
Ultrasound Irradiation ◽  
Reaction Conditions ◽  
Homoallylic Alcohols ◽  
Ultrasound Assisted ◽  
High Yields

Novel homoallylic alcohols incorporating sulfone moieties were synthesized by the treatment of different carbonyl compounds with allylic bromides in aqueous mediaviasonochemical Barbier-type reaction conditions. Sulfonation ofα-bromoketones with sodium benzenesulfinate in presence of CuI/2,6-lutidine rapidly gaveβ-keto-sulfones in good yields. In general, ultrasound irradiation offered the advantages of high yields, short reaction times, and simplicity compared to the conventional methods. The structures of all the compounds were confirmed by analytical and spectral data.

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