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Yoshimura A, Takamachi Y, Han LB, et al. Organosulfide-Catalyzed Diboration of Terminal Alkynes under Light. Chemistry. 2015;21(40):13930-3doi: 10.1002/chem.201502425.
Yoshimura, A., Takamachi, Y., Han, L. B., & Ogawa, A. (2015). Organosulfide-Catalyzed Diboration of Terminal Alkynes under Light. Chemistry (Weinheim an der Bergstrasse, Germany), 21(40), 13930-3. https://doi.org/10.1002/chem.201502425
Yoshimura, Aya, et al. "Organosulfide-Catalyzed Diboration of Terminal Alkynes under Light." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,40 (2015): 13930-3. doi: https://doi.org/10.1002/chem.201502425
Yoshimura A, Takamachi Y, Han LB, Ogawa A. Organosulfide-Catalyzed Diboration of Terminal Alkynes under Light. Chemistry. 2015 Sep 28;21(40):13930-3. doi: 10.1002/chem.201502425. PMID: 26376328.
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Chemistry. 2015 Sep 28;21(40):13930-3. doi: 10.1002/chem.201502425.

Organosulfide-Catalyzed Diboration of Terminal Alkynes under Light.

Chemistry (Weinheim an der Bergstrasse, Germany)

Aya Yoshimura, Yuki Takamachi, Li-Biao Han, Akiya Ogawa

Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531 (Japan).
  2. National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1, Higashi, Tsukuba, Ibaraki, 305-8565 (Japan).
  3. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531 (Japan). [email protected].

PMID: 26376328 DOI: 10.1002/chem.201502425

Abstract

An efficient metal-free diboration of terminal alkynes is reported. In the presence of a catalytic amount of organosulfides under light, the addition of bis(pinacolato)diboron (B2pin2) to terminal alkynes takes place efficiently to produce the corresponding double borylation products in good yields. Mechanistic studies indicate that this metal-free sulfide-catalyzed diboration of alkynes likely occurs by generation of a boryl-centered radical with the aid of light and a sulfide, since such a radical was detected in the reaction mixture by electron spin resonance (ESR) spectroscopy. The present form of catalysis (sulfide/light) is thought to be unprecedented and provides a new means of preparation for organoboranes without heavy metal contamination in the products, which is highly desired in the preparation of drugs and electronic materials.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: alkynes; borylation; organocatalysis; photochemistry; sulfides

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