CuI-Mediated Bromoalkynylation and Hydroalkynylation Reactions of Unsymmetrical Benzynes: Complementary Modes of Addition

Xiao Xiao, Tao Wang, Feng Xu, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Benzynes formed by heating a suitable triyne (or tetrayne) substrate are shown to react with in situ generated alkynyl copper species. The latter are compatible with the polyyne substrates and two types of chemistries have been achieved: (i) 1-bromo-1-alkynes efficiently undergo net bromoalkynylation of the (unsymmetrical) benzynes and (ii) in situ generated alkynylcopper species give rise to hydroalkynylation products. The regiochemical preferences of these two modes of reaction are complementary to one another with respect to the position of alkynyl substituent in the final products.

Original languageEnglish (US)
Pages (from-to)16564-16568
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number50
DOIs
StatePublished - Dec 10 2018

Bibliographical note

Funding Information:
This study was supported by the U.S. Dept. of Health and Human Services [National Institute of General Medical Sciences (R01 GM65597 then R35 GM127097)] and the National Science Foundation (CHE-1665389). A portion of the NMR data were obtained with an instrument funded by the NIH Shared Instrumentation Grant program (S10OD011952).

Keywords

  • alkynylations
  • aryne trapping
  • copper
  • homogeneous catalysis

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