Cooperative Ligand-Promoted P(III)-Directed Ruthenium-Catalyzed Remote Meta-C–H Alkylation of Tertiary Phosphines

Herein, we disclose a ruthenium-catalyzed meta-selective C–H activation of phosphines by using intrinsic P(III) as a directing group. 2,2,6,6-Tetramethylheptane-3,5-dione acts as the ligand and exhibits an excellent performance in boosting the meta-alkylation. The protocol allows an efficient and st...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 6; pp. 2057 - 2062
Main Authors Zhou, Zheng-Xin, Li, Jia-Wei, Wang, Liang-Neng, Li, Ming, Liu, Yue-Jin, Zeng, Ming-Hua
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.03.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
STRATEGY
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Summary:Herein, we disclose a ruthenium-catalyzed meta-selective C–H activation of phosphines by using intrinsic P(III) as a directing group. 2,2,6,6-Tetramethylheptane-3,5-dione acts as the ligand and exhibits an excellent performance in boosting the meta-alkylation. The protocol allows an efficient and straightforward synthesis of meta-alkylated tertiary phosphines. Several meta-alkylated phosphines were evaluated for Pd-catalyzed Suzuki coupling and found to be superior to commercially available ortho-substituted phosphines. The practicability of this methodology is further demonstrated by the synthesis of difunctionalized phosphines.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00237