Direct Use of Phosphonium Salts for Alkylation of p-Quinols: Formal α-Arylation of Carbonyls via a 5-Membered Betaine-Type Intermediate,Organic Letters

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Direct Use of Phosphonium Salts for Alkylation of p-Quinols: Formal α-Arylation of Carbonyls via a 5-Membered Betaine-Type Intermediate
Organic Letters ( IF 4.9 ) Pub Date : 2022-09-21 , DOI: 10.1021/acs.orglett.2c02638
Saddam Husen _{1,

2} , Priyankar Jha ₁ , Akansha Singh _{1,

2} , Ravindra Kumar _{1,

2}

Affiliation

Unlike phosphonium ylides used extensively for C═C bond formation, herein we disclose the direct use of phosphonium salts for site-selective alkylation to p-quinols via a 5-membered betaine-type intermediate. This strategy provides a novel and general approach for the synthesis of α-(m-aminoaryl) esters, amides and ketones under ambient conditions. The reaction proceeds through in situ generation of P-ylide, alkylation and aromatization. Reaction is highly compatible with diverse functional phosphonium salts and amines.

中文翻译：

磷鎓盐直接用于对喹啉的烷基化：通过 5 元甜菜碱型中间体对羰基进行形式 α-芳基化

与广泛用于 C=C 键形成的鏻叶立德不同，本文中我们公开了直接使用鏻盐通过 5 元甜菜碱型中间体进行位点选择性烷基化为对羟基苯酚。该策略为在环境条件下合成 α-( m-氨基芳基)酯、酰胺和酮提供了一种新的通用方法。该反应通过原位生成P-叶立德、烷基化和芳构化进行。反应与多种功能性鏻盐和胺高度相容。

更新日期：2022-09-21

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