The "borrowing hydrogen" (BH) method for C-alkylation reactions using alcohol as alkylating agents is an important synthetic transformation. In this respect, designing cheap and bench stable earth abundant metal catalyst for borrowing hydrogen transformation is a key challenge to be witnessed. Herein we have presented a synthesis of non-phosphine, easily accessible and bench stable SNSÀ Ni complexes. The Ni-catalyst was successfully applied for the C-alkylation of ketone enolates to α-alkylated ketones. Primary alcohol with different functional groups and various heteroaromatic alcohols are well tolerated. The present catalyst system was efficiently applied to gram scale synthesis and also the green chemistry metrics of the reaction were calculated. The present protocol was also extended successfully for the synthesis of biologically important quinoline moieties. Finally, various control experiments and deuterium labelled experiments suggest that the reaction proceeds via borrowing hydrogen pathway.
An
efficient Ru doped hydrotalcite catalyzed N-alkylation of benzamides
and sulfonamides with alcohols via borrowing hydrogen catalysis is
illustrated. Various primary alcohols, including benzyl, heteroaryl,
and aliphatic alcohols, were alkylated in good to excellent yields.
To shed light on the mechanistic details, several control studies
and deuterium labeling experiments were performed. Mechanistic studies
underpin that the reaction is going via a borrowing hydrogen pathway
rather than an SN1 type mechanism. The reaction can be
easily scaled up without any detrimental effect on the yield. The
catalyst is also capable of synthesizing quinazolinone directly from
2-aminobenzamide and alcohols. Successful recyclability and high reactivity
highlight the practical applicability of the catalyst.
At present, alcohols are discovered as sustainable starting materials that can be used in organic synthesis for various organic transformations and the preparation of commodity chemicals. Acceptorless Dehydrogenation (AD) and...
Herein we described the selective synthesis of both alkylated and alkenylated fluorenes using a single SNS ligand derived nickel complex. The protocol was employed for a wide range of substrates,...
Herein, we demonstrate a visible light-induced selenium
radical-mediated
domino reaction of aryl alkynoates, for the synthesis of 1,1-diselenide
alkene derivatives and selenium-containing α,β-unsaturated
carboxylic acid. The process is mild, metal free, easy to handle,
and scalable. The decarboxylation step can be controlled by applying
a catalytic amount of Eosin Y dye and cesium carbonate as a base.
The methodology shows good functional group tolerance and provides
decent yields of the products. In addition, the synthetic utility
of this protocol was expanded further by preparing the allylic alcohol,
α,β-unsaturated ester, and vinylic halides.
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