Ru(II)-catalyzed
direct alkylation of tertiary phosphines via hydroarylation
of activated olefins promoted by mono-N-protected
amino acid (MPAA) was achieved. This protocol provides a straightforward
access to a large library of Buchwald-type bulky alkylated monophosphines
from commercially available biaryl phosphine. Moreover, two ruthenacycle
intermediates of tertiary phosphines via C–H bond cleavage
were isolated to illustrate the mechanism of P(III)-directed C–H
activation.
A regio- and stereoselective iodolactonization of electron-deficient olefinic acids has been reported, which provides a straightforward access to seven-membered lactones with two consecutive chiral centers.
An efficient and straightforward synthesis of arylsubstituted biarylphosphines via unprotected amino acidaccelerated ruthenium-catalyzed P-directed ortho-CÀ H arylation reaction is described. This protocol utilized commercial and inexpensive (hetero)aryl chlorides as efficient arylating reagents under solvent-free reaction conditions. Notably, diverse aryl bromides were also effective for this transformation. With the protocol, a wide variety of monoarylated biarylphosphines were obtained in moderate to high yields and excellent selectivity. Moreover, the arylsubstituted phosphine exhibited higher catalytic performance than its precursor and other substituted phosphines in palladium-catalyzed Suzuki coupling.
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