4.7 Article

Pd-Catalyzed disilylation: an efficient route to 2,2 '-bis(trimethylsilyl)biphenyls via trapping transient dibenzopalladacyclopentadienes with hexamethyldisilane

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 5, Issue 9, Pages 1488-1492

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8qo00189h

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Funding

  1. National Natural Science Foundation of China [21572051, 21602057]
  2. Ministry of Education of the People's Republic of China [213027A]
  3. Education Department of Hunan Province [15A109]
  4. Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University [KLCBTCMR201707, KLCBTCMR201708]

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A palladium-catalyzed disilylation reaction of 2-iodobiphenyls with hexamethyldisilane via trapping transient dibenzopalladacyclopentadienes has been achieved. Diversely functionalized 2,2'-bis(trimethylsilyl) biphenyls have been synthesized in good to excellent yields under mild conditions. Moreover, 2,2'-bis(trimethylsilyl) biphenyls readily transformed into 2,2'-dihalobiphenyls, which could be used to synthesize carbazole, dibenzo[b,d]thiophene and dibenzo[b,d]selenophene polycyclic heteroarenes.

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