4.7 Article

Triphenylcarbenium Tetrafluoroborate-Catalyzed 1,6-Addition of 1-Aminobenzotriazole to p-Quinone Methides: Synthesis of Diarylmethylamines

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 23, Pages 4069-4074

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200953

Keywords

Carbocation-catalyzed; Triphenylcarbenium Tetrafluoroborate; Green Synthesis; Diarylmethylamines

Funding

  1. Taishan Scholars Construction Projects of Shandong [tsqn201812075]
  2. Natural Science Foundation of Shandong Province for Distinguished Young Scholars [ZR2020JQ07]
  3. Youth Innovation Science and Technology Plan of Colleges and Universities in Shandong Province [2019KJC003]
  4. Natural Science Foundation of China [21702115, 21801007]
  5. Natural Science Foundation of Shandong Province, China [ZR2019PB020, ZR2017BB028, ZR2016JL012]
  6. Qingdao University of Science Technology

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A metal-free method for synthesizing diarylmethylamines was developed using a 1,6-addition reaction of 1-aminobenzotriazole with p-quinone methides catalyzed by triphenylcarbenium tetrafluoroborate. The diarylmethylamines were obtained in moderate to good yields (up to 84%) under mild conditions, and showed unchanged activity after 6 reuses.
A metal-free synthesis of diarylmethylamines via triphenylcarbenium tetrafluoroboratecatalyzed 1,6-addition of 1-aminobenzotriazole to p-quinone methides (p-QMs) was developped. Under mild condition, diarylmethylamines could be obtained in moderate to good yields (up to 84%) by simple filtration, showing essentially unchanged activity after 6 reuses.

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