Undirected, Asymmetric Alkyl Group Functionalizations through Alkane Dehydrogenation

作者：Yu, Feng; Tao, Renqing; Su, Yiting; Liu, Guixia^*; Huang, Zheng^*

来源：Organic Letters, 2022, 24(25): 4563-4568.

DOI：10.1021/acs.orglett.2c01009

• C-H AMINATION
• STEREOSELECTIVE FUNCTIONALIZATION
• ALKENE HYDROBORATION
• BENZYLIC BORYLATION
• BONDS
• ACTIVATION
• SECONDARY
• HYDROFUNCTIONALIZATION
• HYDROAMINATION
• METATHESIS

Direct asymmetric alkyl group functionalizations can potentially convert abundant and inexpensive hydrocarbon feedstocks into value-added chiral fine chemicals. Here, we report a one-pot, dehydrogenation-based strategy for enantioselective formal benzylic C(sp(3))-H bond borylation. Dehydrogenation of alkylarenes by a pincer-Ir complex produces aryl alkenes via a tandem dehydrogenation/alkene-isomerization catalysis. The subsequent Cu-catalyzed asymmetric alkene hydroboration affords benzylic boronate esters with excellent site- and enantioselectivity. The generality of this strategy has been further demonstrated by asymmetric alkyl group amination.

• 单位
  中国科学院研究生院