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4.4.6.3.2.2 Reduction of Organic Halides

DOI: 10.1055/sos-SD-104-00776

Yoshida, H.Science of Synthesis Knowledge Updates, (2022319.

After their pioneering work on the generation of aryl or alkenyl anions via a halogen–metal exchange-type process with silylstannane-derived stannyl anions, which attack a carbonyl group intramolecularly,[‌64‌] Mori and co-workers expanded this method of reducing organic halides to related cyclizations,[‌78‌‌82‌] the generation of alkylidene carbenes from 1,1-dibromoalkenes, and the generation of arynes from 1,2-dibromoarenes.[‌83‌] In addition, treatment of 1,2-bis(bromomethyl)benzene with the tributylstannyl anion results in the generation of ortho-quinodimethane, which undergoes [4 + 2] cycloaddition with dienophiles to afford 1,2,3,4-tetrahydronaphthalene derivatives 26 (Scheme 22).[‌83‌,‌84‌]

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