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Rhenium-Catalyzed Regioselective ortho-Alkenylation and [3 + 2 + 1] Cycloaddition of Phenols with Internal Alkynes.
Org Lett. 2019 05 03; 21(9):3441-3445.OL

Abstract

An operationally simple and direct rhenium-catalyzed ortho-alkenylation (C-alkenylation) of unprotected phenols with alkynes was developed. The protocol provided ortho-alkenylphenols exclusively, and formation of para- or multiply alkenylated phenols and hydrophenoxylation (O-alkenylation) products were not observed. The [3 + 2 + 1] cycloaddition of phenols and two alkynes via ortho-alkenylation was also demonstrated, in which the alkynes functioned as both two- and one-carbon units. These reactions proceeded with readily available starting materials under neutral conditions without additional ligands.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Murai M
Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushimanaka, Kita-ku , Okayama 700-8530 , Japan.
Yamamoto M
Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushimanaka, Kita-ku , Okayama 700-8530 , Japan.
Takai K
Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushimanaka, Kita-ku , Okayama 700-8530 , Japan.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

30998367

Citation

Murai, Masahito, et al. "Rhenium-Catalyzed Regioselective ortho-Alkenylation and [3 + 2 + 1] Cycloaddition of Phenols With Internal Alkynes." Organic Letters, vol. 21, no. 9, 2019, pp. 3441-3445.
Murai M, Yamamoto M, Takai K. Rhenium-Catalyzed Regioselective ortho-Alkenylation and [3 + 2 + 1] Cycloaddition of Phenols with Internal Alkynes. Org Lett. 2019;21(9):3441-3445.
Murai, M., Yamamoto, M., & Takai, K. (2019). Rhenium-Catalyzed Regioselective ortho-Alkenylation and [3 + 2 + 1] Cycloaddition of Phenols with Internal Alkynes. Organic Letters, 21(9), 3441-3445. https://doi.org/10.1021/acs.orglett.9b01214
Murai M, Yamamoto M, Takai K. Rhenium-Catalyzed Regioselective ortho-Alkenylation and [3 + 2 + 1] Cycloaddition of Phenols With Internal Alkynes. Org Lett. 2019 05 3;21(9):3441-3445. PubMed PMID: 30998367.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhenium-Catalyzed Regioselective ortho-Alkenylation and [3 + 2 + 1] Cycloaddition of Phenols with Internal Alkynes. AU - Murai,Masahito, AU - Yamamoto,Masaki, AU - Takai,Kazuhiko, Y1 - 2019/04/18/ PY - 2019/4/19/pubmed PY - 2019/4/19/medline PY - 2019/4/19/entrez SP - 3441 EP - 3445 JF - Organic letters JO - Org Lett VL - 21 IS - 9 N2 - An operationally simple and direct rhenium-catalyzed ortho-alkenylation (C-alkenylation) of unprotected phenols with alkynes was developed. The protocol provided ortho-alkenylphenols exclusively, and formation of para- or multiply alkenylated phenols and hydrophenoxylation (O-alkenylation) products were not observed. The [3 + 2 + 1] cycloaddition of phenols and two alkynes via ortho-alkenylation was also demonstrated, in which the alkynes functioned as both two- and one-carbon units. These reactions proceeded with readily available starting materials under neutral conditions without additional ligands. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/30998367/Rhenium_Catalyzed_Regioselective_ortho_Alkenylation_and_[3_+_2_+_1]_Cycloaddition_of_Phenols_with_Internal_Alkynes_ DB - PRIME DP - Unbound Medicine ER -
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