suzuki doc (1995)

Chem. Rev. 1995, 95,2457-2483 2451 Palladium-Catalyz ed Cross-Couplin g Reactions of Organoboron Compounds Norio Miyaura' and Akira Su zuk i'n t DivisMn of Molecukr Chemistry, FacuKy of Engfm~ing, okkaa Univemw, Sappew NO, Japan R W anuary 31 , 1995 (Revised Manmpt Received August 17, lN5) Contents I . lntmduction II. Svnthesis of Omanoboron Reaoents A Synthesis frk Organoliihiim or Magnesium Reagents B. Hydroboration of Alkenes and Alkynes C . Haioboration of Teninal Alkynes D. Miscellaneous Methods Compounds and Their Mechanism A. Cross-Cowlino Reaction 111 Palladium-Catalyzed Reactions of Organoboron B . Oth er Catal yti ; Pro ces s by Transition-Metal Complexes IV. Cross-Coupling Reaction A. Coupling of 1 Alkenylboron Derivatives: Synthesis of Conjugated Dienes 6. Coupling of Arylboron Derivatives: Synthesis of Biaryls C. Coupling of Alkylboron Derivatives D. Coupling with Triflates E . Synthesis of Vinylic Sulfides F . Coupling with lodoalkanes: Alkyl-Alkyl CouDlino G. Coupling with Other Organic Halides and Boron Reagents V. Head-to-Tail Coupling VI. Carbonylative Coupling VII. Alkoxycarbonylation and Dimerization VIII. Conclusion 2457 2458 2458 2458 2459 2459 2460 2460 2464 2465 2465 2469 2471 2473 2473 2475 2475 2476 2476 2478 2478 1 . Introduction The cross-coupling reaction now accessible via a variety of organometallic reagents may provide a fundam entally com mon synthetic methodology (eq 1). R-M + R'-X Ra' 111 I n 1972, Kumada and and independently that th e reaction of organomagnesium reagents with alkenyl or aryl halides could be mark- edly catalyzed by Ni(I1) complex. Kochi3 found the efficiency o f Fe(II1) catalyst for th e cross-coupling o f Grignard reagents with 1-halo-1-alkenes and Liz- CuClr catalyst for haloalkanes. The palladium- catalyzed reaction of Grignard reagents was first reported by Murahashi? th e synthetic utility o f which was then amply demonstrated by Negishi5 o n the reactions of organoaluminum, zinc, and zirconium Pdcataiyal ' esent address: Kurashiki University of Seience and the Arts, Kurashiki 712, Japan. ' 1 Norio Myaura was bom in Hokkaido. Japan in 1946. He received his BSc. and his Dr. from Hokkaido University. He became a research as sffiia te and an asscciate professor o f A. Suzuki's research group and was promoted to the professor of the same group in 1994. In 1981, he joined J. K. Kochi research group at Indiana Universily and studied the catalylic and noncatalyti c epoxidation of alkenes wth oxwmetal reagents. His current interests are mainly in the field of transition-metalcatalyzed reaclions of organoboron compounds, with emphasis on applications to organic synthesis. For examples, cros sco upl ing reaction, cataly tic hydroboration, catalytic thioboration, and catalytic diboration of alkenes and alkynes. Akira Suzuki was born n Ho%ka oo. apan In 1930 He received his undergraduate ana graoLate Iran ng at ho66aido Jniversily and joined the lacully in 1961 as an assistant professor. h e spent two years as a postdoctoral associate w In Professor herben C. Brown a 1 PurdJe Un iver sty ana wa s promoled 1 Ine rank 1 professor in 1971. Alter reirement from Hokkaido Ln'versry. Akira SJZLki moved to Okayama ty Sc as a cnemtstry 1994. His inleresis are m a nly n lne hel a of organ obor on cn em isly . wi th empnasis o n app catlons to organ c syntnes s. organometal IC chemistry, an0 tne study 1 reactive interned ales reagents. After those discoveries, man y other orga- nometalli c reagents have prov en to be highly useful as nucleophiles for th e cross-coupling reaction, e.g., organolithiums by Murahashi: organostannans by Migita' an d Stille? 1-alkenylcopper(1) by Normant? organosilicon compounds by Hiyama.'O These reac- 0009-2665/95/0795-2457$15.5010 0 995 American Chemical Society

suzuki doc (1995)

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