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Traceless Acetal-Directed Catalytic Hydrosilylation of Propargyl Acetates Harnessing the <i>π</i>-Acidic Catalyst.

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(C6F5)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.

SUBMITTER: Dakarapu US 

PROVIDER: S-EPMC12439862 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature

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Traceless Acetal-Directed Catalytic Hydrosilylation of Propargyl Acetates Harnessing the &lt;i&gt;π&lt;/i&gt;-Acidic Catalyst.

Dakarapu Udaya Sree US   Chang Yao Chung YC   Avullala Thirupataiah T   Das Adhikary Suman S   Nguyen Hiep H HH   Jeon Junha J  

ACS catalysis 20240919 19

Traceless acetal-directed, <i>α</i>-specific <i>syn</i>-hydrosilylation of propargyl alcohols has been developed, enabling a synthesis of <i>β</i>-silyl allylic alcohols. An introduction of inexpensive, readily accessible acetal as a traceless, two-atom tether directing group (DG), along with a <i>π</i>-acidic catalyst, facilitates the proximal, <i>α</i>-selective <i>syn</i>-hydrosilylation of a broad spectrum of primary to tertiary propargyl alcohols. Notably, the utilization of a highly fluori  ...[more]