Alkoxyphosphorane/Borane Cooperative Alkylations: A Frustrated Lewis Pair Version of the Mitsunobu Reaction-Reference-Cited by-同舟云学术

Alkoxyphosphorane/Borane Cooperative Alkylations: A Frustrated Lewis Pair Version of the Mitsunobu Reaction

Published:2023-03-15 Issue:23 Volume:29 Page:
ISSN:0947-6539
Container-title:Chemistry – A European Journal
language:en
Short-container-title:Chemistry A European J

Author:

Chen Ting¹^ORCID,Mei Yanbo²^ORCID,Liu Liu Leo²^ORCID,Zhao Yufen¹,Wu Yile¹^ORCID,Stephan Douglas W.¹³^ORCID

Affiliation:

1. Institute of Drug Discovery Technology Ningbo University 315211 Ningbo Zhejiang P. R. China

2. Department of Chemistry and Guangdong Provincial Key Laboratory of Catalysis Southern University of Science and Technology 518055 Shenzhen P. R. China

3. Department of Chemistry University of Toronto 80 St. George St M5S3H6 Toronto ON Canada

Abstract

AbstractThe combination of the alkoxyphosphoranes, Ph2P(OR)(O2C6Cl4) and the borane B(C6F5)3 generates the zwitterions 3 which act as FLP to effect the alkylation of several nucleophiles affording C−C, C−N, C−H and C−Cl coupling products. A DFT study shows the reaction proceeds via an FLP activation pathway generating an alkoxyphosphonium intermediate which effects the alkylation of the nucleophiles, akin to the Mitsunobu reaction.

Funder

Natural Science Foundation of Ningbo

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202300264

Reference41 articles.

1. Preparation of Esters of Carboxylic and Phosphoric AcidviaQuaternary Phosphonium Salts

3. Alkylphosphinites as Synthons for Stabilized Carbocations

4. Mitsunobu and Related Reactions: Advances and Applications

5. Mitsunobu Reaction Using Basic Amines as Pronucleophiles

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