Suzuki reaction - 2026 ACF Regionals

Question

Like the related Buchwald–Hartwig amination, this reaction often uses metal catalysts containing two diphenylphosphine ligands connected via a ferrocene molecule. For 10 points each:

[10m] Name this carbon-carbon bond forming reaction between an organohalide and an aryl or alkyl boronic acid. This reaction’s namesake discoverer shared the Nobel Prize with Richard Heck and Ei-ichi Negishi.

ANSWER: Suzuki reaction [accept Suzuki cross-coupling; or Suzuki–Miyaura cross-coupling or SM cross-coupling or SMC; prompt on cross-coupling reactions or coupling reactions; prompt on palladium-catalyzed reactions or nickel-catalyzed reactions; prompt on organometallic reactions]

[10e] C–C bond formation occurs during the reductive form of this reaction, the last step of the Suzuki catalytic cycle. The E2 type of this reaction outcompetes substitution using bulky bases on secondary alkyl halides.

ANSWER: elimination [accept reductive elimination]

[10h] Ligands with a large value for quantity like diphenylphosphines tend to favor reductive instead of beta-hydride elimination. This quantity does not directly factor in a ligand’s steric bulk, unlike a related quantity introduced by Chadwick Tolman.

ANSWER: bite angle [or omega; prompt on angle; reject “cone angle” or “theta”]

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Summary


California (North)	Main Site	Y	3	20.00	100%	100%	0%
California (South)	Main Site	Y	4	12.50	75%	50%	0%
Canada	Main Site	Y	11	10.00	73%	27%	0%
Florida	Main Site	Y	3	6.67	67%	0%	0%
Great Lakes	Main Site	Y	5	12.00	100%	20%	0%
Lower Mid-Atlantic	Main Site	Y	9	10.00	78%	22%	0%
Midwest	Main Site	Y	8	12.50	88%	13%	25%
Northeast	Main Site	Y	6	11.67	50%	50%	17%
Overflow	Main Site	Y	4	12.50	75%	50%	0%
South Central	Main Site	Y	2	10.00	100%	0%	0%
Southeast	Main Site	Y	8	11.25	75%	38%	0%
UK	Main Site	Y	12	10.00	67%	33%	0%
Upstate NY	Main Site	Y	4	17.50	100%	50%	25%

Data


Berkeley A	Berkeley C	10	10	0	20
Stanford B	Berkeley D	10	10	0	20
Berkeley B	Stanford A	10	10	0	20
Arizona State	UC Irvine	0	10	0	10
UCLA A	UC Santa Barbara	10	10	0	20
UCSD A	UCSD C	10	0	0	10
UCLA B	UCSD B	0	10	0	10
Toronto C	Brock	0	0	0	0
Carleton University	Simon Fraser	0	10	0	10
Guelph	Toronto F	0	10	0	10
Ottawa	McGill A	0	10	0	10
McGill B	Western A	0	0	0	0
McMaster B	Toronto D	10	10	0	20
Queen's	Western B	10	10	0	20
Toronto E	Toronto G	0	0	0	0
Toronto Metropolitan	Toronto B	0	10	0	10
UBC A	Western C	10	10	0	20
Waterloo A	UBC B	0	10	0	10
Central Florida A	Central Florida C	0	10	0	10
Florida B	Central Florida B	0	0	0	0
Florida C	Florida A	0	10	0	10
CWRU B	Michigan B	0	10	0	10
Michigan A	Michigan C	10	10	0	20
Ohio State B	Michigan State	0	10	0	10
Ohio State A	Pittsburgh	0	10	0	10
Ohio State C	CWRU A	0	10	0	10
Virginia	Liberty A	0	10	0	10
Liberty B	South Carolina B	0	0	0	0
North Carolina A	James Madison B	0	10	0	10
South Carolina A	NC State B	0	10	0	10
NC State A	VCU	10	10	0	20
Virginia Tech A	Duke	10	10	0	20
Liberty C	Virginia Tech B	0	0	0	0
Wake Forest	North Carolina B	0	10	0	10
North Carolina C	William and Mary	0	10	0	10
Chicago B	Illinois C	0	10	0	10
Chicago D	Illinois B	0	10	0	10
Chicago A	Indiana A	0	10	10	20
Northwestern D	Indiana C	0	10	0	10
Chicago C	Northwestern C	0	10	0	10
Chicago E	Notre Dame A	0	0	0	0
Illinois A	Purdue A	10	10	10	30
Northwestern B	Purdue B	0	10	0	10
Bowdoin B	Bowdoin A	0	0	0	0
Brandeis A	Brown	0	0	0	0
Dartmouth A	Brandeis B	0	0	0	0
MIT	Dartmouth B	10	10	10	30
Harvard A	Harvard B	10	10	0	20
Yale	Southern Connecticut State	10	10	0	20
Georgia Tech A	Iowa State	10	10	0	20
Minnesota A	Carleton College	10	10	0	20
Missouri B	Missouri A	0	0	0	0
Washington B	Washington A	0	10	0	10
Texas A	Texas A&M A	0	10	0	10
Texas B	Murray State A	0	10	0	10
Georgia Tech C	Alabama A	10	10	0	20
Louisville A	Alabama B	0	10	0	10
Bruin	Tennessee A	10	10	0	20
WashU A	Georgia Tech D	0	10	0	10
Georgia Tech B	Louisville B	10	10	0	20
Kentucky	Tennessee B	0	10	0	10
Mississipi State	Vanderbilt B	0	0	0	0
WashU B	Sewanee	0	0	0	0
Edinburgh B	Birmingham	0	10	0	10
Warwick A	Bristol	0	10	0	10
Cambridge B	Edinburgh A	0	10	0	10
Durham	Southampton A	0	0	0	0
Imperial A	Manchester	10	10	0	20
UCL	Imperial B	0	0	0	0
Montpellier	LSE	0	10	0	10
Cambridge A	Oxford A	10	10	0	20
Cardiff	Oxford B	0	0	0	0
Oxford C	Imperial C	0	0	0	0
City St. George's	Southampton B	10	10	0	20
Cambridge C	Warwick B	10	10	0	20
Binghamton B	Cornell C	0	10	0	10
Cornell A	Cornell B	0	10	10	20
Penn State	Binghamton A	10	10	0	20
RIT	Rochester	10	10	0	20