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. 2023 Jan 7;14(5):1286-1290.
doi: 10.1039/d2sc05841c. eCollection 2023 Feb 1.

A Ni-catalyzed asymmetric C(sp)-P cross-coupling reaction for the synthesis of P-stereogenic alkynylphosphines

Bin Zhang  1 , Wen-Qing Zhou  1 , Xu-Teng Liu  1 , Yingying Sun  1 , Qing-Wei Zhang  1
Affiliations

A Ni-catalyzed asymmetric C(sp)-P cross-coupling reaction for the synthesis of P-stereogenic alkynylphosphines

Bin Zhang et al. Chem Sci. .

Abstract

Due to the high reactivity of the triple bond, P-stereogenic alkynylphosphines could be easily derivatized, serving as universal building blocks for structurally diverse phosphine compounds. However, the synthesis of alkynylphosphines via direct P-C bond formation was unprecedented. Here, we report an efficient method for the synthesis of P-stereogenic alkynylphosphines with high enantioselectivity via a Ni-catalyzed asymmetric cross-coupling reaction. The reaction could tolerate a variety of functional groups, affording products that can be converted into useful phosphine derivatives.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. P-stereogenic alkynylphosphines.
Fig. 1
Fig. 1. (A) Hydration. (B) Radical addition cyclization. (C) Synthesis of P-stereogenic phosphepine. (D) PL spectra of 6 in THF/water mixtures with different water fractions and 6 films under 365 nm. (E) CPL spectra of 6 films. (F) glum value spectra of 6 films.
See this image and copyright information in PMC

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