Abstract
Most homogenous gold catalyses demand ≥ 0.5 mol% catalyst loading. Owing to the high cost of gold, these reactions are unlikely to be applicable in medium- or large-scale applications. Here we disclose a novel ligand design based on the privileged (1,1'-biphenyl)-2-ylphosphine framework that offers a potentially general approach to dramatically lowering catalyst loading. In this design, an amide group at the 3'-position of the ligand framework directs and promotes nucleophilic attack at the ligand gold complex-activated alkyne, which is unprecedented in homogenous gold catalysis considering the spatial challenge of using ligand to reach anti-approaching nucleophile in a linear P-Au-alkyne centroid structure. With such a ligand, the gold(I) complex becomes highly efficient in catalysing acid addition to alkynes, with a turnover number up to 99,000. Density functional theory calculations support the role of the amide moiety in directing the attack of carboxylic acid via hydrogen bonding.
Original language | English (US) |
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Article number | 3470 |
Pages (from-to) | 3470 |
Number of pages | 1 |
Journal | Nature communications |
Volume | 5 |
DOIs | |
State | Published - 2014 |
Bibliographical note
Funding Information:We appreciate the financial support of NIH (NIGMS (R01 GM084254), NSF (CHE-1301343) and the Natural Science Foundation of China (Grant number 21172248, 21121062).