Three-Component Reaction to 1,4,2-Diazaborole-Type Heteroarene Systems
Dr. Jun Li
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraβe 40, 48149 Münster, Germany
Search for more papers by this authorDr. Constantin G. Daniliuc
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraβe 40, 48149 Münster, Germany
Search for more papers by this authorDr. Gerald Kehr
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraβe 40, 48149 Münster, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Gerhard Erker
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraβe 40, 48149 Münster, Germany
Search for more papers by this authorDr. Jun Li
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraβe 40, 48149 Münster, Germany
Search for more papers by this authorDr. Constantin G. Daniliuc
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraβe 40, 48149 Münster, Germany
Search for more papers by this authorDr. Gerald Kehr
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraβe 40, 48149 Münster, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Gerhard Erker
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraβe 40, 48149 Münster, Germany
Search for more papers by this authorGraphical Abstract
The reaction product between the bulky FmesBH2 borane and an isonitrile serves as a B/N frustrated Lewis pair that adds nitriles to form the dihydro-1,4,2-diazaborole heteroarene derivatives. One example of this class of compounds was shown to undergo a cycloaddition reaction with N-phenylmaleimide.
Abstract
The borane FmesBH2 reacts in a three-component reaction with an isonitrile and a small series of organonitriles to give rare examples of the class of dihydro-1,4,2-diazaborole derivatives. In a related way, annulated BN-indolizine derivatives became conveniently available, as were dihydro-1,4,2-oxaza- or thiazaborole derivatives. The nucleophilic framework of a dihydro-1,4,2-diazaborole example allowed for an uncatalyzed acylation reaction. It also served as a 1,3-dipolar reagent and underwent a [3+2] cycloaddition/[4+2] cycloreversion sequence when treated with methyl propiolate to give the respective pyrrole product. The [3+2] cycloaddition product of a dihydro-1,4,2-diazaborole derivative with N-phenylmaleimide was isolated and its heterobicyclo[2.2.1]heptane derived structure characterized by X-ray diffraction.
Conflict of interest
The authors declare no conflict of interest.
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