Substrate‐Assisted, Transition‐Metal‐Free Diboration of Alkynamides with Mixed Diboron: Regio‐ and Stereoselective Access to trans‐1, 2‐Vinyldiboronates. Issue 18 (29th March 2017)

• Record Type: Journal Article
• Authors: Verma, Astha; Snead, Russell F.; Dai, Yumin; Slebodnick, Carla; Yang, Yinuo; Yu, Haizhu; Yao, Fu; Santos, Webster L.
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 18(2017)
• Page Start: 5111
• Page End: 5115
• Publication Date: 2017-03-29
• Subjects: alkenes -- boron -- chemoselectivity -- cross-coupling -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201700946
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A substrate‐assisted diboration of alkynamides using the unsymmetrical pinacolato‐1, 8‐diaminonaphthalenato diboron (pinBBdan) is described. The transition‐metal‐free reaction proceeds in a regio‐ and stereoselective fashion to exclusively afford trans ‐vinyldiboronates in good to excellent yields. Notably, Bdan and Bpin are installed on the α‐ and β‐carbon atoms, respectively. Abstract : Who needs metals? Transition‐metal‐free diboron activation with alkynamides facilitates the intramolecular formation of differentially protected trans ‐vinyldiboronates. The reaction proceeds in a regio‐ and stereoselective fashion with Bdan and Bpin installed on the α‐ and β‐carbon atoms, respectively. dan=1, 8‐diaminonaphthalene, pin=pinacol.