Synthesizing Substituted Bicyclo[1.1.1]pentane via Transition Metal Catalysis

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Solution Overview

Problem

The commercialization of bicyclo[1.1.1]pentane derivatives is hindered by their high cost and low yields in synthetic organic chemistry, limiting their availability and application in fields like pharmaceuticals and advanced materials due to challenging and inefficient synthesis methods.

Innovation Solution

A method involving the combination of [1.1.1]propellane, a Group VII or Group IX transition metal compound, a hydride source, and a reagent to substitute bicyclo[1.1.1]pentane, allowing for the synthesis of substituted bicyclo[1.1.1]pentane compounds, which can include various substituents, thereby overcoming the limitations of existing synthesis routes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If known synthetic schemes are used to prepare bicyclo[1.1.1]pentane derivatives, then the compounds can be synthesized, but the synthesis is costly and yields are low

Engineering Contradiction:

Improvesynthesis yieldVSAvoidsynthesis cost

Core Design Contradiction:

ProductivityVSEase of manufacture

Solution Approach 1:

The patent changes the reaction parameters by using [1.1.1]propellane as a starting material with transition metal catalysts and specific reagents, transforming the synthesis pathway to achieve higher yields and lower costs compared to known synthetic schemes

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent employs transition metal compounds (Group VII or Group IX) as intermediaries/catalysts to facilitate the substitution reaction of bicyclo[1.1.1]pentane, enabling more efficient synthesis with improved yields and reduced costs

Inventive Principle:

Principle #24Intermediary (Mediator)

2Adaptability or versatility

If known synthetic schemes are used to prepare bicyclo[1.1.1]pentane derivatives, then the compounds can be synthesized, but the availability of reagents is limited

Engineering Contradiction:

Improvereagent availabilityVSAvoidsynthesis efficiency

Core Design Contradiction:

Adaptability or versatilityVSProductivity

Solution Approach 1:

The patent employs a universal synthetic approach using [1.1.1]propellane as a common starting material that can be transformed into various substituted bicyclo[1.1.1]pentane derivatives through different reagents, enhancing both reagent availability and synthesis efficiency

Inventive Principle:

Principle #6Universality (Multi-functionality)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This approach enables the production of substituted bicyclo[1.1.1]pentane compounds with improved efficiency and reduced costs, expanding the chemical space for exploration in pharmaceuticals and other fields by providing more cost-effective and accessible building blocks.

Implementation Method 1

combining [1.1.1]propellane; a Group VII transition metal compound or a Group IX transition metal compound; a hydride source; and a reagent capable of contributing all or a part of a substituent group

Methodology Applied

Scientific EffectCatalysis: Catalysis

Data Source

PatentUS10189780B2Bicyclic alkyl compounds and synthesis

Publication Date: 2019.01.29 RECURIUM IP HLDG LLC

AI summary

Disclosed herein are compounds of the general Formula (I), and methods of synthesizing a substituted bicyclo[1.1.1]pentane using a Group VII or Group IX transition metal compound.