Details

Autor(en) / Beteiligte

• Li, Yangyang
• Pang, Hailiang
• Wu, Dong
• Li, Zheqi
• Wang, Wang
• Wei, Hong
• Fu, Ying
• Yin, Guoyin

Titel

Nickel‐Catalyzed 1,1‐Alkylboration of Electronically Unbiased Terminal Alkenes

Ist Teil von

• Angewandte Chemie International Edition, 2019-06, Vol.58 (26), p.8872-8876

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2019

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• An unprecedented nickel‐catalyzed 1,1‐alkylboration of electronically unbiased alkenes has been developed, providing straightforward access to secondary aliphatic boronic esters from readily available materials under very mild reaction conditions. The regioselectivity of this reaction is governed by a unique pyridyl carboxamide ligated catalyst, rather than the substrates. Moreover, this transformation shows excellent chemo‐ and regio‐selectivity and remarkably good functional‐group tolerance. We also demonstrate that under balloon pressure, ethylene can also be utilized as a substrate. Additionally, competence experiments indicate that selective bond formation is favored at the α‐position of boron and preliminary mechanistic studies indicate that the key step in this three‐component reaction involves a 1,2‐nickel migration. An unprecedented alkylboration of electronically unbiased terminal alkenes, featuring 1,1‐regioselectivity, was achieved by using a novel nickel catalyst. This reaction provides remarkable regioselectivity without the assistance of coordinating groups. Moreover, it exhibits excellent functional‐group tolerance and chemoselectivity toward monosubstituted double bonds.