Work

Traceless Acetal-Directed Catalytic Hydrosilylation of Propargyl Acetates Harnessing the π-Acidic Catalyst

Year: 2024

Type: article

Abstract: Traceless acetal-directed, α-specific syn -hydrosilylation of propargyl alcohols has been developed, enabling a synthesis of β-silyl allylic alcohols. An introduction of inexpensive, readily accessible acetal as a traceless, two-atom tether directing group (DG), along with a π-acidic catalyst, facilitates the proximal, α-selective syn -hydrosilylation of a broad spectrum of primary to tertiary propargyl alcohols. Notably, the utilization of a highly fluorinated, π-acidic Rh(I)/P(C 6 F 5 ) 3 catalyst allows rapid cyclizing syn -addition of a silicon–metal species across a C–C triple bond via a strong M-π interaction. A postmodification of the resulting cyclic silyl acetal not only removes the DG, rendering it traceless, but also introduces a functional group to the silicon moiety, enhancing the versatility and utility of the products.

Source: ACS Catalysis

DOI: 10.1021/acscatal.4c04132

Authors: Udaya Sree Dakarapu, Yao Chung Chang, Thirupataiah Avullala, Suman Das Adhikary, Hiep H. Nguyen, Junha Jeon

Institution: The University of Texas at Arlington

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green