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Updated: Jun 17, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

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[1.1.1]烯与卡特里茨基二烯盐的光诱导多元组分异构结合

Yulin Xiao1, Jianyang Dong1, Yuying Wang1

  • 1Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, People's Republic of China.

Organic letters
|August 14, 2024
PubMed
概括

研究人员开发了一种新的方法,使用轻量级和易于获得的原材料制造功能化的bicyclo[1.1.1]pentanes (BCPs). 这种方法可以有效地合成复杂分子用于药物发现.

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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