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a biotage 5 ml microwave vial containing a stirring bar was charged with [ rh(acac)(co2 ) ] ( 2 mol % , 4.3 mg , 0.0166 mmol ) , ( r , r)-ph - bpe ( 3 mol % , 12.6 mg , 0.0249 mmol ) and paraformaldehyde ( 6 equiv , 150 mg ) . the vial was sealed with a crimp cap , purged with three vacuum / argon cycles and left under an argon atmosphere .
alkene ( 150 mg , 0.832 mmol ) , toluene ( 3 ml ) and an internal standard ( 1 drop of cyclooctane ) were added to a schlenk flask under an inert atmosphere .
the resulting solution was mixed , and a small sample was taken for a t0 nmr analysis .
the solution was then added to the microwave vial and heated to 120 c using microwave radiation .
after 45 min , the vial was cooled , and the positive pressure inside the vial was released by piercing the cap with a needle .
a small sample was taken and analysed by h nmr spectroscopy to calculate the conversion to the resulting aldehyde .
the aldehyde was reduced using nabh4 to the corresponding alcohol ( see the supporting information ) and isolated using flash chromatography on silica gel ( n - hexane / etoac 4:1 ) to give 2,3-diphenylpropan-1-ol as a white solid ( 126 mg , 0.60 mmol ) .
the enantiomeric excess of the alcohol was determined by chiral hplc on a chiralcel od - h , 2504.6 mm , n - hexane/2-propanol 90:10 , 0.5 ml min , 254 nm , tr[()-(r ) , major]=18.3 min , tr[(+)-(s ) , minor]=20.5 min ; [ ]d 85.5 ( c 1.0 , chcl3 , ee 95 % ; lit : [ ]d 80.7 ( c 1.13 , chcl3 ) , ee 93 % ) see the supporting information for nmr data . caution ! ! !
this procedure gives enhanced convenience and requires far less complicated safety measures than conventional ahf , because the syngas is added to the reactor in solid form .
using the amounts above , the highest pressure detected during an athf using 6 equiv of [ ch2o]n was 7 bar at reaction temperature ( 4 bar at rt ) .
the highest pressure detected at 120 c when no athf was taking place , but decarbonylation did was 13 bar .
in the 50 ml glass or steel pressure vessels , the highest pressure detected was 3 bar .
similar to the majority of chemical reactions with volatile components , scale - up of these procedures needs careful consideration of the pressures possible and the maximum operating pressure of the vessel used .
as a service to our authors and readers , this journal provides supporting information supplied by the authors .
such materials are peer reviewed and may be re - organized for online delivery , but are not copy - edited or typeset . technical support issues arising from supporting information ( other than missing files ) should be addressed to the authors
as an alternative to conventional asymmetric hydroformylation ( ahf ) , asymmetric transfer hydroformylation ( athf ) by using formaldehyde as a surrogate for syngas is reported . a catalyst derived from commercially available [ rh(acac)(co)2 ] ( acac = acetylacetonate ) and 1,2-bis[(2s,5s)-2,5-diphenylphospholano]ethane(1,5-cyclooctadiene ) ( ph - bpe ) stands out in terms of both activity and enantioselectivity . 
 remarkably , not only are high selectivities achievable , the reactions are very simple to perform , and higher enantioselectivity ( up to 96 % ee ) and/or turnover frequencies than those achievable by using the same catalyst ( or other leading catalysts ) can be obtained by using typical conditions for ahf .