Microwave-Promoted Metal-Free alpha-Alkylation of Ketones with Cycloalkanes through Cross-Coupling of C(sp(3))-H Bonds

The microwave-promoted alpha-alkylation of ketones with cycloalkanes as alkylating agents under metal-free conditions is presented. The reaction mechanism involves the DTBP-initiated (DTBP=di-tert-butyl peroxide) microwave-assisted formation of the required cycloalkyl and alpha-ketone carbon radical...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 6; no. 10; pp. 1445 - 1450
Main Authors Wang, Qian-Qian, Wang, Zhang-Xin, Zhang, Xin-Ying, Fan, Xue-Sen
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.10.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
alkanes
ACTIVATION
METHYLENE
1,3-DICARBONYL COMPOUNDS
radical reactions
CARBONYL-COMPOUNDS
C-H FUNCTIONALIZATION
ALCOHOLS
microwave chemistry
cross-coupling
SIMPLE ALKANES
CHEMISTRY
alkylation
OLEFINS
DERIVATIVES
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Summary:The microwave-promoted alpha-alkylation of ketones with cycloalkanes as alkylating agents under metal-free conditions is presented. The reaction mechanism involves the DTBP-initiated (DTBP=di-tert-butyl peroxide) microwave-assisted formation of the required cycloalkyl and alpha-ketone carbon radicals followed by a selective cross-coupling step. This is the first example in which simple ketones and 1,3-diketones have been efficiently alkylated with cycloalkanes under metal-free conditions through the cross-dehydrogenative coupling of C(sp(3))-H bonds. Compared with previous methods, this alkylation protocol has advantages such as the use inexpensive and abundant substrates under metal-free conditions and its good atom-economy and sustainability. Moreover, the substituted ketones can be used as intermediates in the preparation of the synthetically and biologically valuable trisubstituted alkenes.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201700256