4.8 Article

Catalyst-Enabled Chemodivergent Construction of Alkynyl- and Vinyl-Substituted Diarylmethanes from p-Quinone Methides and Alkynes

Journal

ORGANIC LETTERS
Volume 21, Issue 18, Pages 7539-7543

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02810

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Funding

  1. National Natural Science Foundation of China [21572065, 21772042]
  2. Science and Technology Commission of Shanghai Municipality [18JC1412300]
  3. Program for Changjiang Scholars and Innovative Research Team in University [IRT_16R25]

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Here, a catalyst-controlled chemodivergent 1,6-addition of p-quinone methides with alkynes was developed, affording diverse alkynyl- and vinyl-substituted diarymethanes. In this transformation, copper catalyzed the direct 1,6-addition of p-QMs with alkynes, while iron promoted the three components reaction of p-QMs, alkynes, and halogens from iron salts or added FIX acid. The salient features of this transformation include completely controllable chemoselectivity, mild conditions, inexpensive catalysts, and good substrates scopes.

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