Kazufumi Shibata

Nickel‐Catalyzed Homoallylation of Aldehydes and Ketones with 1,3‐Dienes and Complementary Promotion by Diethylzinc or Triethylborane

Regio- and stereoselective homoallylation of saturated aldehydes and ketones to give bishomoallyl alcohols 1,3-anti-1 is achieved with [Ni(acac)2 ] (cat.) and Et2 Zn [Eq. (a)]. This new catalyst system thus complements the previously reported combination of [Ni(acac)2 ] with Et3 B, which offers advantages in the homoallylation of unsaturated and aromatic aldehydes. acac=acetylacetonato.

Pd·Et3B-catalyzed alkylation of amines with allylic alcoholsElectronic supplementary information (ESI) available: experimental section. See http://www.rsc.org/suppdata/cc/b2/b210920d/

A combination of catalytic amounts of Pd (0.05 mmol) and Et3B (0.3 mmol) promotes allylic alkylation of primary and secondary aromatic and aliphatic amines (1.0 mmol) by the direct use of allylic alcohols, providing tertiary amines in excellent yields under mild conditions (room temperature approximately 50 degrees C).

Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds.

Linear 1:1:1 coupling of dimethylzinc, 1,3-dienes, and carbonyl compounds in this order is facilitated by catalytic amounts of [Ni(acac)(2)] to give (E)-3-hexen-1-ols in good yields under mild conditions [Eq. (a)]. Increasing steric hindrance at the carbonyl group favors formation of the 1:2:1 adduct, and this is the sole product when the carbonyl compound is acetone. acac=acetylacetonate.

Ni0-catalyzed regio- and stereoselective coupling reaction of Me3B, isoprene, and aldehydes

Abstract In the presence of Ni(acac) 2 (0.1 equiv.), the three components of trimethylborane, isoprene, and aromatic and aliphatic aldehydes combine to produce 1-substituted 3-methyl-3-hexenols ( 3 ) in good yield and with high regio- and stereoselectivity ( E : Z >13:1).

Nickel-catalysed three-component connection reaction of a phenyl group, conjugated dienes, and aldehydes: stereoselective synthesis of (E)-5-phenyl-3-penten-1-ols and (E)-3-methyl-5-phenyl-3-penten-1-ols

Abstract In the presence of 10 mol% of Ni(acac) 2 , Ph 2 Zn reacts with 1,3-butadiene and aldehydes at room temperature to give 1-alkyl and 1-aryl substituted ( E )-5-phenyl-3-penten-1-ols ( 3 ) in good yields. Under similar conditions, the three components of Ph 3 BZnEt 2 , isoprene, and aldehydes combine with each other to furnish 1-alkyl and 1-aryl substituted ( E )-3-methyl-5-phenyl-3-penten-1-ols ( 5 ) in good yields.