Formation of a Hybrid 1-Bora-3-boratabenzene Heteroarene Anion Derivative
Dr. Qiu Sun
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Search for more papers by this authorDr. Constantin G. Daniliuc
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Search for more papers by this authorDr. Christian Mück-Lichtenfeld
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Search for more papers by this authorDr. Gerald Kehr
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Gerhard Erker
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Search for more papers by this authorDr. Qiu Sun
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Search for more papers by this authorDr. Constantin G. Daniliuc
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Search for more papers by this authorDr. Christian Mück-Lichtenfeld
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Search for more papers by this authorDr. Gerald Kehr
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Gerhard Erker
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Search for more papers by this authorGraphical Abstract
The unique synthesis of a boryl-substituted borole system by means of a 1,1-hydroboration/1,1-alkenylboration sequence provided access to the unprecedented 1-bora-3-boratabenzene class of compounds.
Abstract
The B(C6F5)2-substituted borole 2⋅SMe2 was obtained from the phenyl bis(trimethylsilylethynyl) borane SMe2 adduct (1⋅SMe2) by a synthetic sequence containing a rare 1,1-hydroboration reaction. Subsequent thermolysis at 50 °C converted it to the bicyclic borenium/borate zwitterion 3⋅SMe2. Photolysis of 3⋅SMe2 gave the diboracyclohexadiene derivative 4⋅SMe2, which after ligand exchange with N,N-dimesitylimidazolylidene and deprotonation gave the 1-bora-3-boratabenzene anion derivative as its potassium salt 6. Some unique follow-up reactions of the unsaturated diboron containing six-membered heterocycles were investigated.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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